I bought my John Deere 270 5 years ago for $9k with 4300 hours. It was in very nice condition for its age and hours and had garaged for the last 10 years of its life(prior to the unknown). It did have a few issues and even before getting it home, I had it taken to a repair shop for a once-over. The seller took care of the towing and I paid for the service. Nothing major needed to be addressed, so I had them do a fluid/filter service and tracking adjustment on one drive motor. When I got it home and compared it to my neighbors NH LS170, it was HUGE. Apparently it is a "large frame" skid steer. Who knew there were different size framed machines, I thought skidsteer is skidsteer. Nope. His is little, maneuverable, quick, easy to get in and out of. Mine is none of those! Mine weighs near 10k#, lifts 3000# and is a beast. During my ownership I've had to repair a leaking oil cooler($350), radiator repair($300), replace tires($900), replace miscellaneous hoses/fiittings(couple hundred $), replace a steering pump piece($400), water pump/belt/tensioner($500), wheel studs($50), lift arm pins/bushings($350) and lots of fluids, filters, nuts & bolts. I've kept a detailed log of all the expenditures including accessories and attachments purchased over the years. All-in to date I'm at around $25,000 which included $3400 for rubber OTT(over the tire tracks). That sounds like a lot and would have been if it wasn't spread out over 5 years. The attachments, pallet forks $718, stump bucket $659, rock bucket $949, backhoe/grapple $2603, tracks $3400 and snowplow $975.
When we were first considering buying a skidsteer, she needed to know whether it was a worthwhile investment or if I just wanted a new toy. Fair enough. She's a CPA and way over-analyzes everything and I'm the total opposite. I was able to justify it to her and she sort-of agreed that it might be a worthwhile machine to have around. Now that it's been part of our lives, she's 1000% a believer in having it around. It was funny, a few months ago while her brother was visiting, the garage doors were open and he commented on how much "stuff" was in there. He said that I should get rid of "stuff" that I don't use, like the skidsteer and Jen quickly said, "no way, he uses that all the time"! Way to go honey!!!!! That's my girl!!!!
I have saved over $100k, maybe $150k doing my own work at the property rather than hiring out to a contractor. Probably would have cost me $20k to rent machines and attachments when I need to do a project. It's worth having it here when I need it. If I come home from the shop and decide to work for a few hours it's here. I picked up a pallet of rock salt on Monday, drove home, pulled out the JD, lifted the whole pallet out of the pickup and put it in the garage. Could I have unloaded all fifty 50# bags by hand, carried them in the garage and restocked them? Yep, but at 56, it gets a bit more difficult as the years roll by. The biggest thing so far was doing all of the landscaping and hardscaping around the property. I've done so much stone and boulder work when I want and how I want that I couldn't imagine life without it. I did have an issue a few years back during a very wet spring/summer/fall where it continued to get stuck every time I was off the hard packed driveway. It took some saving, but I opted to add rubber tracks over the tires to help with "floatation". They work very well but do have some mechanical shortcomings if you abuse the machine or drive/maneuver on pavement as mentioned by jgrewe. They are also fantastic for plowing.
Anyway, that's a bit of my take on skidsteers. Oh and my machine is worth twice what I paid for it nowadays! All-in-all a fantastic investment so far.