MT:  "Since I will be spending the first 5 days or so in Quetico and wandering up toward Basswood falls that would certainly put me at odds with the "spirit" of the entry system would it not?"

While I tend to agree with your logic, and think the day paddle on day in and over night paddle #71 on day back into BWCA is correct, outfitter said just get the overnight paddle to start with and it will be fine until you "leave the wilderness".  I don't like to circumvent laws because you won't get caught, but lets say you got a #71 that started two days before you crossed back into US. No USFS ranger will stop you in Q and they won't know when you are in US when you entered, and you've not deprived them of any money, so?

My direction recently has been to get the overnight paddle and paddle up Moose the night before Q rather than bunk and pay for a tow to PP. One of those 4-5 sites near top of moose and a couple of minutes from PP is nearly always open - if not all of them - and while not perfect, it's economical and all perfectly legal.