It is not that bad on the road except for a few select cities such as:
The biggest concern you'll need regarding your equipment is the ability to properly perform pre-trip inspections and during trip inspections.
The second biggest concern you'll need will be the ability to properly maintain tire(tyre) pressures as faulty tyre pressures will certainly enable you to NOT complete a journey and sometimes even maintaining tyre pressures tyres may pop when their time is due, yet this does not happen too often if one has the ability to properly inspect ones equipment and advise for maintenance when needed.
My wife drove for 1 1/2 years before getting out of the driving field and she did not have any problems with truck tyres yet as most of us do and will , she had all sorts of problems with trailers.
There seems to be the complete and utter nonsense inherent in trucking of not checking trailer tyres before proceeding upon ones journey because either "it takes too much time" or "someone else will do it" whereupon NO-ONE ever does until the tyre repair shop does(ANYONE can do it, SOMEONE might, yet NO-ONE wants to). Yes, i'll admit that it does take a weeee bit of time to do especially while in the rain or during the winter yet the probability of being stuck waiting for tyre repair versus checking the tyres yourself is what kept me checking EACH and EVERY trailer I pulled thereby also ensuring that the next driver had well pressured tyres.
Just something I liked to do when I was driving long/short haul.
I would also crawl underneath(weather permitting) to check wheel seals, and also check wheel bearing lube by removing hub cap plug unless the hubs were of the sealed type.
There are quite many responsibilities included in trucking in addition to "just driving".
Talk with your son about these needs and see if he does not concur.
BEst WELLness to you and yours in ALL ventures!!