Do whatever you want, I own both tractors and skidsteers, a dozen or so tractors, two skid steers, I tell everyone you can take my tractors, but nobody is taking my skidsteers anywhere, they'll be the very last piece I'll ever part with, just my opinion, now that said do some searching on the web at auction prices, and look at what dealers and jockies are asking in your area. I know what you mean about because you want one, some things in life don't make economic sense, I can certainly understand that, I've got sheds full of those purchases.
Now to help narrow your search somewhat, you've been given some idea's to go off of, I'd venture one further, rent a machine for a weekend, or several machines for several different weekends, call it a test drive and find out what you like or dislike, no different than finding a vehicle or anything else, ask for a demo on your property if possible, then look around and find out who sells and services what, locally, brands mean nothing if you can find parts or someone to help you out when your knuckle deep in oil and totally out of idea's how to fix it or what's wrong, service is key in my opinion, then parts, brands mean nothing to me.
If you plan to fix it yourself and do your own repair, maybe look at older one's instead of newer one's, they have less electronics on them and depending on the make and model, are easier to fix, your not going to wear anything out anyhow, it'll save you some bucks.
If nobody has told you this, machines are addictive, its almost a disease, so says my wife, collecting them and attachments are something that never ends its just a beginning, just make sure whatever you get, it has auxillary hydraulics on it, the single most important thing on any skid steer, if you go with a tractor, a three point, pto and hydraulics are needed
