OP, you're in a similar situation I was in 4 years ago. I bought a piece of land that needed some work done and I also owned a bunch of heavy shop machinery (lathe, Bridgeport, welding tables, etc) that I needed to move to the shop on said new property. I grew up in a family owned JD Dealership, then when my dad retired he sold Bobcat for a bit and now is selling Deere again. I've been around machinery and agriculture / construction my entire life so I feel like I have reasonable exposure to give some guidance here.
Back in '20, my dad talked me into buying an early 2000s Bobcat T190. It has a vertical lift system, hand and foot controls, but has enough aux flow to run some small attachments like an auger or the brush mower that I made from an old bushhog. It was a great decision. Parts are all still easily available and the controls are cheap and simple to work on. Hand and foot controls are better for a machine that isn't an all day production machine and that you don't want to dump a ton of money into if you have to replace a joystick. Easy manual adjustments, no computer calibrations, and actual feedback from the pumps. If you are finding that your ankles are sore at the end of the day, try wearing lower top shoes like hiking boots instead of half calf. Also, keeping the rocker and linkage bushings in good shape in the pedals and rods is important. As they wear, it takes more motion to operate the controls and it reduces the control resolution when cutting grade. $30 in bushings and 45 minutes of work will make a HFC machine operate like a dream again. Also, if you're a bigger person, you won't like HFC because of just general ergonomics.
Tracks vs tires... my experience is that tire machines are for improved or semi-improved surfaces and tracks are for going off in the mud and woods. Yes, tracking over roots sucks in a track machine because every damn bogie gives you a bump, however the stability and overall traction is much better. Tires will get you stuck on wet clay though. Track maintenance is expensive but for MY usage, its worth it. I'd have turned over and sank a tire machine several times using it the way I use my CTL.
I spent 9 hours in my T190 yesterday helping a friend clean up some property and tear up a plywood addition on an abandoned house on some property he bought. The machine spent the day tearing, crushing, carrying and loading a revolution of dump trailers. My ankles are fine and I have MS and I'm 40... I am leaving the house here in a minute with the same machine to go move a bunch of backfill at a friend's brewery where they are building a shop themselves and its time to finish the grade.
I've put some time and work and parts into this machine, but I have also put 790 hours on it in 4-1/2 years working on my property, the family farm, and helping out friends like yesterday and today.
In regards to buying new machinery - financing can be weird with buying it as a personal thing and not a business. I bought a '24 Bobcat E48 cab mini-ex back in March (after pricing and looking at Tak, Deere, CAT, Bobcat, Yanmar, and Develon,) and Bobcat was the best match for my personal use and overall cost point for a roughly 5T mini. I know a lot of people hate Bobcat but I hate Kubota equipment (even though I do like their engines, such as the one that is in this T190). A lot of people Hate Bobcat but its a decent mid-level machine at a mid-level cost. Its not junk, but its not super HD commercial CAT.
Its also amazing the tasks I come up with for the machine.
