Considerations would be having to have a CDL or not, Class A or B, hazmats, air brakes, regular medical condition screening, etc. Lots of delivery folks of all disciplines of articles are using p/u trucks with bumper pull for light loads like commodity deliveries to grocery stores (rather than vans) or goosenecks for heavier things, especially construction materials around here. Since larger P/U type chassis are becoming popular, load sizes can be increased and you have the upkeep of a p/u, not of an OTR tractor-trailer. CDLs aren't required for these here......as I recall.
If your plan is to run OTR then you need accommodations on the truck, even if it's only a bunk behind the seat on a cabover. Back in '90 when I was looking, Coke-a-Cola was selling single axle, "daytime" cab chassis combination tractors, 250 range HP, for $6k just a few years old with very low miles, well maintained.....passed as I was doing rock bucket work and needed 400+HP and tandem axle.
I had all of the above at one time and were terminated when the state found out I was no longer driving....ok since I'm 77 and don't need nor want to.....and by their doing that, I wasn't tempted to do things like you are suggesting.
Another thing is road rage. P/U chassis is a different mind set and you aren't posing the same obstacle to the average driver of a low to the ground sedan, shiny new this or that, hot rod, etc. Some people just go nuts when a semi pulls out in front of them, or they come upon one on the roadway.