I'm in the same boat. As a one man show, I only have limited time. I think if I have to upgrade trucks, I may get a 450 or 550 and get a bigger trailer. I had my trailer derated at the factory to stay under CDL. Sounds silly but it saved me a lot of time and hassle but if I want to grow to where I can take on bigger work, then I will need bigger equipment. A mini x with 14k breakout would open a lot of doors in the rock moving department. As for stumps, I rather grind them down and haven't come across much that's too big for my 335. It's the rocks and being able to dig and carry and place. That's where a bigger machine would shine but by the time I add up everything, I better have a lot of work to support that since I'd need to update trucks, trailers, and complimentary tools like my dump trailer. Wouldn't make much sense to have a CDL and bigger truck and only have a 14k dump trailer. I'm not worried about testing. I have a college degree. My issue is I don't have anyone close to me with a class A to go with. My trucker only has a Class B so I'm not sure what to do about that part plus nothing I own would allow me to take the test. Right now, I'm attachment poor but if I got into a bigger excavator with better hydraulic performance, I might get several attachments for it and get out of the skid steer more often. I think a 6 ton machine would open some doors on road work that's been typically reserved for the backhoe or small dozer in this area. I have done difficult work with my little Bobcat 335 and can imagine doubling my productivity with a bigger machine.