Understandably a major pain for him is needing to have a reliable form of transport at the same time as having to learn new skills and make time available for tinkering.
If I were in that frustrating position, and had a few extra bucks, I might get something like a Honda C-90 for reliable transport, taking the pressure off for the learning/tinkering/trial-and-error phase of motorized bicycle skill acquisition.
The 21 million C-90s were made! They're simple, bullet proof, get 120 mpg, and reportedly can use vegetable oil in place of motor oil, if necessary.
Honda c90 : C90 Pictures