I have many hours in them. A wheeled machine is much better on smooth surfaces, a track machine floats over smaller bumps. But as others said, driving a tracked unit down a road, you are just asking for problems. Just a few miles on tar, and you will see the damage on the tracks.
$for$ you will get a bigger machine with tires. Tracks are nice, but they are also a lot more maintenance, and expensive to maintain.
Wheel units can get stuck easier in mud, but if you get a tracked unit stuck in thicker clay mud, and a track falls off, you just found yourself some good manual labor, unless you have a larger machine to dig, and pull the machine out. If you have ice, and a slanted driveway, a track steer will teach you how to butt pucker really quick.
Tracks are nice, but if you can do the job with wheels, it will cost a lot less.
Also wanted to add, I think you will need to add at least $10k to your budget to get a larger machine. Brands dont matter much, but just make sure you have a dealer close by, they will, and do break down. If you have to pay someone for repairs, the closer the better. If you have to run for parts, the closer the better. If all things are the same, I would take a Cat 10 out of 10 times.