I agree with all those who voted trailer first, and it sounds like that is the way the OP decided to go… smart! But I really want to know where all of you guys with arenas found someone to do it for $20K!!! (I am expanding the existing small sand arena on my place and the quote is double that… and that was the “best” estimate I got…)
I’m with Heinz 57. For me, an arena is more important much more often than a trailer. Maybe, like Heinz, that’s partly because I have many friends who could haul for me in a pinch. And maybe it’s not a fair comment for me to make because I already had a (cheap) trailer when I moved to my property that didn’t have an arena. But for me, the ability to ride every day was (and is) really really important.
So my vote would be beater trailer that you can use in an emergency, and start as much work toward an arena as you can afford.
are you talking an indoor arena? I would think that would be much more than a run about trailer. Footing alone would be several thousand.
I too vote trailer. I can’t imagine having horses at home and not being able to move them if need be. You don’t need an arena in order to ride but you do need a trailer in order to haul 
Plus this is an odd either/or- way different price points unless you’re getting a super fancy trailer.
If you keep your tack in the trailer, all you need is to to is hooking up the trailer and loading the horse. With experience, it takes less than 10 minutes to do both. Yeah, it is less aggravating if you can just ride at home, but if you really think through the whole process logically, you will most likely find that unless you have $$$$ to throw at your arena, none of which will be recuperated when you sell the property, and can afford to hire help, you won’t save much time or gain more riding opportunities if you get an arena at home.
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We are over 3 hours from a decent vet so we’ve always had a trailer. Before we had a decent arena or when it is flooded or unusable, I ride in the pasture. It may seem difficult since it isn’t level but it does teach them to pick up their feet. I’ve competed at lower level eventing doing this and it hasn’t hurt my dressage at all.
