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JMBT

Sledge said above, "But at least with trucking I can be more valuable by owning my own equipment."

YES, YES, and double YES!!! You can be a company driver and have next to no responsibilities pertaining to truck maintenance, load booking, business finance,..etc. Or you can step up to the plate, become an O/O and do the same job,(burn hours of your life moving shi#t down the road) but do it for 3, 5, hell if you get really specialized with your own equipment, 10 times the money in your pocket! Now, of course you are taking on much, much more responsibility. When the truck breaks down on the roadside and it is 12 degrees outside, you can't just phone the company dispatcher to send a tow truck and relax in a hotel room on hourly pay while it gets fixed. However it sounds like you can manage your money and I would be willing to bet you are the kind of guy that can learn what it takes to keep a truck running, so I would say, as I tell many I talk to on the road. If you are going to make trucking a career, you will build a lot more wealth in the long run if you become an O/O. ...And I wouldn't hesitate, time spent behind the wheel for someone else is making them wealthier by the mile.
As far as the truck, MY OPINION ONLY, I have 18 years as an O/O and have owned 5 trucks. The first was a worn out freightliner that I gave $15,000 for, and wore out a second time saving the money to get a newer truck, but it made $$$$$. Money that I squirreled away any chance I got. The second was a brand new truck, and then another, and then.....The last 2 have been powered by EPA mandated bullshit that they call motors. The infamous 871 and the even worse "updated" 2250. Talking to the 2350 guys, it looks to me like they are just continuing to get worse and more complex, which makes it harder for the common guy to fix. Hell without Rawze's help, through his you tube channel, I would have already been f@3ked! There was a time when I would have sworn the newer truck was definitely the way to go, but those days are loooonnnggggg gone! Older, well taken care of ,or better yet already redone, easier to work on or learn to work on, is your best bet! If you are not running Cali, I would buy 2003 or older. There are literally steals to be had on these trucks in the states! 95's - 99's, 2000's anything with an N-14, or even 02's, 03's, 04's that have the first model ISX's. But here's the gitter....find one that has already been redone, and taken great care of. Do a bit of searching they are not that hard to find. My buddy sold a 94 international with a big bunk last year that he had owned since new...22 years, It literally looked and drove like a brand new truck rolling down the road! Everything had been touched, some things multiple times, but with 2.6 million it was mechanically immaculate! Truck brought 35K at an online sale. I saw a 95 359 Pete online the other day frame up restoration, and pics to prove it asking 39K. I have seen many 2000-2003's cheap as well!
If you are running Cali, you will be in a different boat, just like the rest of us, and in this case I would strongly recommend trucks with the 871, as opposed to the 2250's, 2350's. Simpler in my book is nearly always better. More components mean more things to fail, and if you are just learning about wrenching on them, it will be easier to learn!! Less trips to the shop= more in your pocket!!! Just my 2....take it with a grain of salt!