I’ve been loosely considering selling a 2yr old since spring. I have been talking to a woman who has been interested but she’s very wishy washy and so am I so in the meantime the horse has had some training and has attended a HB show and did very well. Not to mention I’ve put a few extra thousand dollars into veterinary care (she knows.) Is it fair for me to increase the price? How do I go about having that conversation?
She hasn’t given you any money. She is a non factor.
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It is absolutely your prerogative to increase the price. It’s probably best to notify interested parties, but that’s really all. You don’t NEED to justify it, but you can if you want.
“Hello Potential Buyer, Pookie’s price is now $X firm, subject to increase with training. She did really well at the show and has been coming along nicely! I plan to list her again at this price but wanted to let you know before I did. If you’re still interested at the new price, please let me know.” Or something along those lines. Or just “PB, Pookie’s price is now $X. Please let me know if you’d like to move forward.”
If the Potential Buyer gets upset, just thank them for their interest and block. You’re allowed to ask what you want, change that at any time, and do so for any reason.
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I am not sure there is a need for a formal conversation.
The horse has increased in value while this person has not bought it.
Just tell them that very thing - Dobbin has done so well at the trainers and showing that their value has increased by quite a bit. I am advertising to the outside world at $X (whatever your new price is plus a bit), I am willing to sell to you for $Y (Very slightly less, but still more than the previous price).
Edit to add - I like how @fivestrideline worded it better than how I did it. Go with what they said.
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Unpopular opinion, but… i don’t think you need to flag this to them at all. If they were seriously interested, they would’ve vetted the horse, come to see him/her, put down a small deposit, SOMEthing.
I have people who have been telling me they want a custom foal out of my mare for a number of years, i just respond politely, thank them for their interest/comments on her pictures, etc., and i’ve even had conversations in the past with them about how custom foal contracts work, what it would cost, etc. The price i quoted one person back in early 2023 is not what it would cost them now - my mare has produced two more foals since then, so she is much more proven as a broodmare. But i don’t feel compelled to reach out to them and tell them that. 
If you are actually serious about selling, then put an ad up with the increased price and the horse’s accolades/training experience.
Talk is just that - talk. I have lots of people DM’ing me telling me how much they love my mare and what she produces and saying “i really would like a baby from her someday!”. That’s nice and appreciated, but it means nothing and i don’t owe them anything.
Until a contract is signed, a deposit put down or a vetting has been scheduled and has happened, their interest is no different than someone " 
ing" your 2 yr old’s picture on Facebook.
Just sayin’!
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As a buyer of a baby, I would find it perfectly acceptable for the price to change. The seller spending money on vet fees wouldn’t be compelling information You can leave that part out. Just say “I’m listing the 2yo at $___” if she ever asks.
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Times have changed but 30+ years ago, before Internet was so pervasive and online communication available I was engaged in letter writing and telephone communications with a breeder 5 hours away from me regarding a 2 year old colt she had for sale and other youngstock I ‘might’ be interested in. There was an advertisement with price in the Chronicle journal that I was responding to and I spoke to the breeder on the phone the evening before I drove to go see said colt and other available youngstock (we had been in communication over the course of 3 weeks). I made it clear that the colt was at the top of my list based on pictures she sent me and our conversations. The price from first contact to the evening before going to see him was always the same until I drove the 5 hours there. When I looked at all 3 prospects I did land on that colt being the one I was willing to pay for…no need for a PPE, he more or less got one with my visit that day (I’m a vet). I was willing to pay the first $1000 in cash and the remainder via personal check which I would wait for it to clear before returning with a trailer. At that moment she told me her ‘partner’ had told her a few days earlier that the colt’s price was now $4000 higher for no specific reason. It was halter broke and knew things that a typical 2 year old would but never sent out for training or was a trainer hired to come in and train said colt. I was livid because I might not have come to see the horses at all had I known the ‘new’ price and there was definitely opportunity to have told me the night before I spent the gas and time. I learned later that she really wanted me to buy the mare who I was never really interested in but agreed to view because “I might know another breeder who’d be interested if I thought the mare would suit her interests/needs”. I did tell her before I left that she would not hear from me again because I didn’t appreciate the way she conducted business, not a huge loss to her but the breeds we both dealt in were/are very small in number and the typical market for each of us similarly small/limited. Social media didn’t exist then but if anyone asked me about her since we lived in neighboring states and still both active in both breeds for many years got my unadulterated and unembellished opinion of the way she and ‘her partner’ conducted their business. Moral of the story, being honest and forthcoming usually does more to protect your reputation but it’s up to you whether you let this individual know about the price increase no matter how legitimate/justified.
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