Extremely. You are very generous in sharing your priceless horse.
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Just pull her off the horse. She has already shown you she is annoying flaky has no consideration for you and is trending to want to be more ambitious with your horse
Pull her off and tell trainer he is for beginner kids only. You don’t need this woman in your horse life and you can’t invent enough rules in advance to cover all the stupid things she can think up. $200 a month is not enough to have to deal with a perpetual inconsiderate cow.
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When someone tells you who they are, believe them comes to mind …
I would consider telling her horse is off limits, you, OP, will ride him and little kids will in lessons.
Is best for horse, he is getting old and that is all you want him ridden, end of conversation.
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I think your plan is a good one @saitou_amaya. If you don’t mind letting her ride once a week in a lesson with your trainer, then I don’t think there is anything wrong with letting that continue. Honestly it would keep good will between you and your trainer to allow her continued use of your horse for this woman’s lessons. Sounds like you have a good plan to compromise with everyone and not be taken advantage of anymore. Sometimes you do have to pull the plug completely with someone, but it can sometimes work more in your favor to be kind while also setting ground rules. Sounds like a win-win to me.
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my two cents worth would be to be sure she understands about grooming, and make sure she doesn’t freak out about a text.
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That’s all I need to know. She’s retired (presumably, at her age) and can manage her days and time more readily than those of us still working. She’s annoying me, and it’s not even my horse.
She reminds me of my former tenant who was only going to undergrad (no working) and she agreed to hay and check water for my guys in the AM during the week. She had nothing going on in the morning, her wholly online classes didn’t start until 11 every day. She would’ve save 150/month off her rent, dropping it to 650 for her and two ponies at my place.
Guess who consistently couldn’t make it the 200’ from her door to the barnyard every day? YEP. Somehow she just couldn’t do it. So her rent went back up and I fed my own horses. She only fed hers once a day, around 4pm at the earliest (They were on a dry lot). And she wanted to be a vet…
Just stop it. The horse can be used for the tots, and the rest of the time he’s yours.
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That’s very reasonable. And make sure to tell your trainer as well! Mondays only, no rescheduling due to the rider or trainer moving the lesson. You’re not comfortable with him going to shows either, but you’re happy to let him continue to teach her on Mondays. If she wants to do a lease, y’all can talk about it - but it will be Mondays and one other specific day, no exceptions. And no shows. He’s earned his retirement 
Set those boundaries early and firmly, with both trainer and rider, and don’t budge. Be kind, but firm.
And YOU are allowed to change your mind, in any direction!
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If you are going to let this lady ride your horse in a lesson for free (which is a highly unusual arrangement,) make sure she knows that the horse is to be put away spotlessly clean and comfortable with whatever care you would offer him yourself (back massage? treat scratches? Feed lunch? Whatever you do for his additional comfort) and your tack and equipment is to be cleaned also. I’d be a picky witch about that stuff, personally. If she doesn’t like it, well…
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I think that is reasonable, as long you put the kibosh on the local shows. IMHO, showing your aged your horse is really crossing the line at this point in time.
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I’m planning to have a conversation with her and outline how things will work going forward. She can continue to ride him in her lesson on Mondays, but only Mondays and if she cannot make her lesson on Monday and wants to move it to a different day, that won’t work. Horse will not be available any other days for additional rides unless she wishes to resume her lease. In which case, we will resume a month by month lease of $200. And she needs to stick with two specific days of the week without constantly changing them. That sounds reasonable right?
Infinitely reasonable. It locks down the real purpose of letting someone else ride your horse which is to say: you’re not looking for a lease for a financial reason (thereby keeping the door closed to negotiating how many miles/much wear someone puts on him, the idea that someone who was so touchy about being asked to make sure she took care of him properly, wants to take him off property to show??? feels incredibly presumptuous to me). You want someone to ride him to keep him fit. Locking her into her lesson is fair. If she wants to ride him a second day, she must A. resume the lease agreement (it sounds like she gets far more out of riding your guy than she gives back) and B. Lock into a consistent second day (which again, meets what you wanted to get out of a lease: your guy stays in work, keeps fitness up).
Your horse, your rules. Engrave that into your psyche right now.
The idea that she hied off in a snit after you politely asked her to make sure she attends him properly before putting him away really leaves me with a sour taste in my mouth. You were asking for basic attentiveness to horsecare to be adhered. The fact the fallout is as a result of that is demented to me. If she doesn’t like the deal you’re offering now, so be it. Your horse, your rules, and your guy deserves someone who cares enough about the details of his wellbeing to make sure it’s taken care of.
Give her what you suggest above and she can take it or leave it. If she leaves it: that’s on her, and she’s losing out on a sweetheart deal because you sound incredibly reasonable and very easy to work with, and your horse is a great fit for her needs. Don’t let anyone pressure you into thinking you need to compromise or offer more.
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I stopped a riding relationship on my Old Man because the person wouldn’t wipe the bit off. Even after I asked her specifically to do that, just that, only that, in regards to tack cleaning.
I think you’re being so so reasonable letting her ride him in her lessons. But hold her to the rest of the standards, too.
Honestly after a few of the other things you’ve said about flaky, I would hesitate on any lease.
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I think you have been very generous while you were unable to ride. Now that you can ride, you have every right to enjoy your horse. It sounds to me like this is an access issue rather than a monetary issue, excacerbated by the fact she wants to take him to shows.
Personally, I’d tell her you appreciated her help in the past and that you’ll let her know if there are times in the future when it would be helpful for her to ride him again and then end the arrangement.
Edited to add, I once ended a lease agreement when I arrived to ride my horse and found the lessor riding. It wasn’t his day but he complained it was too hot on his regular time. I had hired a babysitter so I could come ride my horse. He thought I was mean. I thought he was entitled.
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OP everyone is giving you great advice.
Let me smack some reality to you in numbers. Rate for 2x a week lease at my barn is about 1,200/month - that is with 2x/weekly lessons. about $850/mo for 1 lesson and 1 hack per week. This includes pro-rated board, shoes, hay, etc.
Granted they’re former CIC star level eventers, but my lease is 22 this year.
HARD NO - the lady was getting away with highway robbery for $200/mo of 2x a week rides.
YOUR horse, YOUR liability, YOUR ride time. Hell no. Have your trainer use him in lessons NOT for said lease lady OR hire someone to hack him when you can’t make it out & the kiddos aren’t lessoning.
As an AA I love hacking people’s oldies before or after my lessons to help them out - even just W/T.
Horse gets cleaned / bathed, fly sprayed, acceptable owner approved treats in their feed pans, stretched, all tack cleaned and neatly put away including bit cleaned off, bridle figure-eighted, fleece girths cleaned with dawn and dried if summer months and sweaty, hand walked and grazed by me, and blanketed / fly sheeted, if needed. Hell I’ll even toss baby pads in the barn laundry if ya want.
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If she doesn’t6 show up on her assigned day to ride, the answer is “No, you can’t ride Sunday instead, I have plans”. Nothing else. Just Nope. Even if your plans are to hand around leaning against the wall watching him eat grass. Its your horse, your time. If she can’t get it together to ride on her assigned days, that’s it. Say “NO”.
Also, make it cleqar to her that if she doesn’t put the horse back according to your instructions, spotless, in other words, that’s the end of the lease, period. And she can’t get insulted by a text. She should decide now if she’s going to play nice and interact like an adult, frankly.
Also, you need to be clear that you will be asking for a lease of x money to ride in a lesson and x money for a second day, agreement ahead of time, per month, no changes from month to month, and that he is put away spotlessly clean, etc. etc. I personally would NOT let him go to a horse show. Far too much can happen there which you are NOT being compensated for. Learning to say “No” is something I feel you should take a hard look at, OP.
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As a rule, I try not to have anything to do with people that are inconsiderate and don’t play well with others, like that lady seems to do in this situation.
Best to take horse back for yourself, keep her out of the picture.
Why?
She has been, is being a thorn in your side about your horse.
Maybe she is starting to lose sense of what is right, but that is not your problem.
Is your horse and your time to enjoy in your way, not accommodate others at your cost.
Is ok to do what you want with your horse, do it. 
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He’s your one in a million, senior horse. Do what is best for him and yourself. This woman seems to do what is best for her. You owe her nothing. Taking her off of your horse is reasonable.
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I’m with Bluey here.
This woman is flaky, a little peculiar in her sensitivity, and is actively trying to stretch what she can get from this situation - changing riding dates, wanting to show, and presumably wanting to take him off site to show (which feels like a big deal to me). And wanting to do this for either free or cheap.
She is not going to change.
I think he should lesson with beginner kids, full stop. If he needs to be ridden more due to your temporary absence, have Trainer do it.
Tell the trainer no more lessons to anyone other than kids. Tell the woman: “I’ve decided to pull Dobbin from any use or lease outside of beginner lessons for children with Trainer. Thanks for your interest, but he is no longer available.”
And that’s it. If she comes back with wheedling texts or backdoor information comes to you from Trainer or a mutual barn friend, just say “Thanks for letting me know. This present course of action is best for Dobbin.”
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OP I lease my horse and I understand your situation!
My situation is with a kid though. The kid helped me out by leasing my pony. It was a win win. The parents are great and have become friends and they will do whatever I say as far as the care of the horse.
The pony was injured and because I’m a big sucker for kids who need a horse to ride, I let her switch to my daughters horse. Then we moved barns, kid only rides about once a week, pays a very low lease rate compared to what the horse is worth IMO. But it works well- they take care of the horse when we are gone and are very respectful of us as the owners. I can’t stress this enough because I tried to partial lease to a kid before and the kid did not listen to me at all- only listened to the trainer.
Pony is now back at our barn. This is my ride. I didnt get to ride for almost a year and I’ve been paying for 2 horses between my pony and my daughters horse. Now the lessor is riding more, her and pony are like peas and carrots and showing and doing great… and I’m back to rarely getting to ride. So… obviously I cannot take pony away from the kid. But now I am clear about saying there are times when I’m riding him and they need to work around me. Its like everyone forgot its my horse. They are going to split some costs leading up to shows cause otherwise, their shows are actually costing me.
Meanwhile, this is great for the trainer- she is making money off the pony with more lessons and show fees. She loves the pony! But the trainer is also very good building back his strength and stuff like that.
It’s never a straightforward situation it seems and we have to decide where to draw the line.
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IMO, it would also clarify if everyone paid:
the trainer for using your horse,
the leaser and
you.
“You” meaning when you can’t ride, but horse needs exercise, you pay for that.
Even just the act of putting a price on each thing helps to see who is taking advantage of whom.
At some barns, trainers who come in to teach have to pay the barn to use the ring, even though the barn has no resident trainer in that discipline. So, everything costs.
You might find getting you’re horse ridden everyday by light weight riders(the kids) costs $10 an hour to you.
Then you might charge the trainer $10 for the use of your horse, so it would be a even exchange.
Now how much would you pay to have the senior ride your horse when you’re away.
So, now what would you charge her for leasing? It should be the same.
If you’re struggling to put $ s on each of these, then take a second look at who is getting the best deal.
You don’t have to any of this but it can be a useful tool for getting perspective on the situation.
Boundaries are key here.
If he’s used in lessons, you require compensation and insurance.
If he is being leased, you require compensation and insurance.
If he is being taken to shows, you require compensation and insurance.
NONE of this should be coming out of your pocket.
You need a contract and you need it now. She needs to pay you for the use of your horse, and the instructor/trainer needs to pay you for the use of your horse. No reduced board as you can be taxed on that. Pay full board, and have the instructor pay you back the agreed upon amount per month of use. None of what you’ve done is unreasonable. What your trainer is doing is sketchy and fraudulent, and the older lady is taking advantage.
Be firm. Set boundaries. He’s your horse, you can do what you see fit.
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