Scope all dealers within 50mile radius of you to see what your service/repair options are first. You don't have to buy local but you will always want to have repairs/parts/etc within short distance. Kioti, LS, Branson, TYM, & Mahindra would probably be the frontrunners. So far, I've owned two Kiotis and love them. I actually preferred LS, but my Kioti dealer was WAY closer if I need any parts or repairs that I can't manage myself. Convenience of your dealer will be a factor like it or not unfortunately. Branson & TYM are probably the least expensive in the lineup but both make good tractors; followed by LS/Kioti. I steered away from TYM when I bought my compact because at the time they only came with Yanmar engines that basically required a dealer to diagnose - I believe many of the new TYM's come with Kukje engines now so these would also be a STRONG contender!). Mahindra is also solid but will usually be a smidge more in price. Poke around on craigslist and see if any of your local dealers offer package deals (including a trailer if you need one to haul in for maintenance/repairs etc). After you find the best 24-29HP tractor that fits your needs at the right price - pop on it. My personal rule is: "If you can put a belly-mower on it, it's an overpriced lawnmower!" but depending on your property, one of the sub-compacts may work for you. On 25-29hp compacts, you're probably not going to get a full package with trailer for under 20k though.
If you want any implements other than the tractor/loader/trailer - usually better to bundle up front instead of later since you can typically get a better deal when you package in some other basic necessities besides just the tractor/loader/trailer (box blade [BB], rotary cutter [RC], post hole digger [PHD], tiller, etc.) - And don't forget the pallet forks - ABSOLUTE LIFE SAVER! For that size tractor you can find a cheap middle buster for <$200 all day online so no need to finance that (very handy for running new underground electric/water lines etc). You may also find a better deal on a RC or BB used on CL (have found many smaller units <$500 each). If you ever think you will need a backhoe... weigh out the cost to buy Vs. rental in the long run. If any neighbors own one - have as many BBQ's as possible & make good friends with them! I've found that I definitely need one and will be getting one soon after considering the numerous times I've had to hand dig halfway to China!