Connor, I think you are getting in way over your head with a new skid steer. Unless your are going to use it more than 5 days per month, you may be better off renting a machine.
I think your best bet is to wait until the end of May/beginning of June after you've made your Spring money and buy a nice used machine in your area. I know I have had several decent used bobcat 753/763/etc. and Case 1845c for $5000- $11000.
If you really want to buy new you should look into getting a Kubota B or L Series tractor with a loader and backhoe which you can get for $18,000-$30,000 brand new with a warranty and payments. I love Kubota tractor's, better then every other in my opinion, even those Green machines. (Even though I will be buying JD mowers this year).
There is an Old Blue Chair for each and every one of us, we just have to find it.
2006 GMC Sierra 2500hd crew cab
BOSS 8'2" Power V
Hustler X-one 60"
Toro Proline 36" wb w/t-bar controls
JS46 22" walk-behind (wouldn't recommend)
Shindaiwa T254, Echo trimmers, chainsaws, pole hedge trimmer, pole saw, hedge trimmer
Shindaiwa 633 and Husqvarna 130BT blower