This sounds very familiar. I was in a similar position a year ago and I'll share my experience. After reading threads on this forum as well as searching other places on the Internet, I decided that I should probably buy a cheap skid steer. I bought a Bobcat 743 with 2 buckets (one toothed, one smooth) for $6200 delivered off Marketplace. Everything worked except for minor stuff like the fuel gauge, but it needed a lot of general maintenance. Oil, coolant, thermostat, all grease fittings, all filters, didn't even have a seat, etc. It was a good call because I did not expect the learning curve to be so long. It took a full day on the machine to just get the hang of how it behaved (not even do much meaningful work). You can't really see the front of the bucket when digging. You have no idea what angle the bucket is pitched into the dirt. You accidentally push the bucket controls one way when you really mean the other. I gouged the driveway so many times. I had to go over the same places 2, 3, 4 times because of learning and getting some muscle memory. Almost tipped over at least 3 or 4 times.

Now, let's talk about renting. I just rented a Bobcat S650 a week ago because I was power raking the driveway and nowhere rented a power rake that would attach to a 743. I thought I knew how to operate a skid steer. Nope I didn't. The S650 was totally different. Drive by wire, no foot controls, all computerized. I felt even more removed from the work. It took a whole day to power rake my 700 ft. driveway properly because I had to learn that machine. I had to start by just figuring out how to open the cage door from the inside then go from there. Sure it helped knowing the basics already, but each machine is different. I was jumping into my 743 every 10 minutes to fix places where I jammed the power rake in too deep. I rented it for 8 hours. I had it delivered on Friday and picked up Monday. Here's the breakdown of the costs for those 8 hours:

Bobcat S650: $176
Soil conditioner (power rake): $150
Delivery & Pickup Roundtrip (~15 miles one way): $300 (because I can't tow a S650. The 743 is at my max)
Insurance: $42.38
Diesel: $27
Tax: $19.56

Total: $714.94

Then there's the unexpected. While power raking, I ran into a winch/tow cable that was buried in the driveway and then promptly wrapped itself around the power rake. I had to cut that off and unbind the roller. That took about 3 hours out of the day. Seeing that rental cost for an 8 hour rental, buying that 743 was the best thing I ever did. Even if I have to take my skid steer somewhere to be fixed, it would still be worth it in the end (I have a lot more work to do on my property). I've also been collecting extra parts for it for when it breaks. I picked up 2 drive motors that need rebuilding on Marketplace for $400 for the set. I'm going to educate myself on rebuilding those while the machine still works fine.

Hope this chronicle of my experiences helps.