I hear ya partner, but I have to add this. If there was going to be any rotting or mold and such from the existing tar paper (along with the possiblity of an interior vapor barrier), I'd suspect that Tom would 'see' that. (Then, maybe not unless he starts looking 'under' the paper ...)
Anyways, what I want to add is that assuming there are 2 barriers now, the house would breath 'better' with vinly up (as apposed to the masonite) because of the 'loose-fitting' vinyl. I do agree that (if the existing paper is in good condition), NOT to add an additional wrap to the house. For the sake of all things being equal, (interior barrier + existing tar paper + vinyl), that's OK. The same principal would apply if Tom were to end up with interior vapor barrier + wrap + vinyl.
I guess w/o knowing if there's an interior barrier, and w/o knowing the condition of the structure & sheathing, I/we can't direct him as 'exactly' as we'd like. That's why I say assuming the house is 'breathing' well (after you inspect it when the masonite is off), leave well enough alone if it's in good condition AND if the vinyl mfgr. say's it's OK w/them (for whatever reason.) I guess to say it another way, if it's gonna be recommended to rip off the tar paper, he/I/we ought to be sure of what's under there and what its condition is before giving him the 'possibility' of unnecessary work. I'm sure you see what I mean. It is worth Tom's time to inspect the outside a bit more after the old siding is removed to see if leaving it is OK. I'm sure that the vinyl mfgr. will have no problem with house wrap assuming he takes off the tar paper.