I highly recommend checking out www.horsetrailerworld.com. You can put in your search criteria and brands you want to look at. Consider a three horse, as resale is better and the extra storage is always nice!
We have an ‘03 Featherlite three horse 13’ LQ, that we were able to pick up in your price range. I did put five new tires on it immediately, but anticipated that when negotiating the price. All in all, we spent less than $26K on an all aluminum LQ trailer, with a huge bathroom, dinette and large fridge. Ours also has a hayrack and mangers, and is 8’ wide, which adds a lot of space. Our first stall has a stud panel, which makes it nice for hauling hay, a wheel barrow and various other things, but keeps the horses from getting at it.
Not all living quarters trailers come with a generator. I have a portable Honda 3000, which will run both my fridge and ac. I very rarely need the generator as most places we camp have electric hook ups. Our refrigerator is a three way, meaning it will run on propane, battery or electric. I run it on the battery while we are traveling, and usually electric while camping.
Look for older (2005 or older) trailers that have been well cared for. They were better built back then. While I love the two older Featherlites we own (we have a stock trailer too), the quality of their new trailers does not impress me.
Trade in values offered are always less than retail. If you can sell privately, you will almost always do better than trade in. Spring is the best time of year to sell, as people are getting itchy to get out and about after winter.
And the Congress starts this week- always a great place to trailer shop if you are anywhere near Ohio!