your post was quite long, and as a result, i started falling asleep reading it...but from what i was to ascertain, you like driving, SMALLER vehicles....
driving a big rig through many of those cities/towns you once did with your car or mini van or SMALL delivery vehicle, IS NOT THE SAME as driving an 18 wheeler......
you cannot easily back them up or turn them around. you have "height issues" and "lenght issues" with big rigs.
its a whole new ball game with an 18 wheeler. i strongly suggest that you go for a refresher course. IN FACT no company will hire you since you have ZERO experience since you originally got your license. as for being on the road, you will get worn out real fast. you WILL NOT be stoping at hotels/motels for your sleep/rest. you WILL BE living in that truck...
sorry to hear that some people close to you have since died....but i hardly find that reason enough to want to be a truck driver. its either something you want to do because you want to, or its something you DO NOT want to do...life/death situations are not any reason to get into trucking, you would be sorely mistaken.
i would rather personally recommend that you stick with class B driving jobs since you stated that you
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"My favorite job EVER was as a courier for Larson Express, of Chicago [small package pickup and delivery, in my own car], which I loved. I got to drive a lot, worked independently, usually didn’t know where I would be going next, and got to think on my feet all the time."
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this way, you'll not get discouraged with driving an 18 wheeler, simply because you "love to drive".......because its a JOB with more responsibility than you could ever imagine........