I have worked in "lower tech"" fields and have worked extensively with trucking companies, so I can somewhat relate to what you are saying and agree it is a bigger obstacle than people in tech give it credit for. However, it is also a nice business opportunity for a software team to build a really important product. Somebody should be able to get VC funding for this. BTW, in my experience, once someone wins this business and a trucking company is using your software, if you don't screw it up badly, you are locked in for a LONG time.