ZippyNH

A freight pilot and CDL holder here... I drove during a industry downturn for a few years....and actually drove for almost 7 years doing a couple years of OTR, but mostly running a day-cab as a USPS contractor, was actually a great break, and it was nice having a "regular" family life for a few years.
Guess it's going to come down to your flexibility, and how much time you can take a pay cut. Honestly, I made similar $$ as a driver/ typed ATP turboprop captain....this will be generally true at MOST flying jobs going from Union CDL teamsters position to a flying job until you get to a "major" or are off probation as a captain at the better paid regionals (not counting one time bonuses that come and go).
At your experience level, you might be able to to buy enough multi engine time to start at AMF (with a few more hours) in the accelerated captain program, but the exact path will be up to you....do you keep building hours, and honing you basic skills (it appears you are making a reasonable wage, and are buying time at a good clip) or keep your $$, and use your savings to supplement you income for a few years..
This is largely a lifestyle/family question... family? Kids? Car/house payments? Supportive spouse? Flexibility to move or be away from home for months at a time?
Yes, trucking and flying cargo has some parallels, the pressures, and to a certain extent the lifestyle (more OTR than day-cab), and having management being at a distance....but there are some difference that you will need to decide if the change in quality of life merit's the pay change in you case.
Anything you do at this point is going to cost you time or $$$....so careful evaluate you options. Heck...you might even find cargo suits your personality better than the airlines.
Sorry for not having a clear cut answer, but there are so many variables, everything from flexibility with the family (most AMF routes are NOT commutable, so the plane you start in, based on experience will limit you base locations...the be-99 is likely as you first PIC aircraft, ACP or new hire captain with some time) to skill level, since some people that have owned planes sometimes have many hours, but can be weak in skills or knowledge...and they all affect the choices.
If it's you dream, it's certainly an option once you get a few more hours of multi engine time, and honestly, the skills and judgement you learn flying cargo is priceless....for some of us, it become a career choice fully unto itself, for others just a stepping stone.
The biggest plus...the only texting idiots swerving in front of us are the ones we see on our commute to/from home/hotel.... likewise I still smile when I look down at traffic jams!
I would suggest you read a few pages back in the thread, there is lots of info, much of it should be helpful in making a choice.