Okay, after a bit of fiddling, I think I worked out a plan to fully repair the mansion and buy the windows by the end of Episode 7 while still retaining the VIP pass (though I'm skeptical Madame is worth the effort). I plan to test it tomorrow, but I figure I'll toss it out now to see if anyone else finds any bugs.
As you might expect, we're going to need to reroll for specific jobs
a lot. So it's definitely not for the faint of heart. I also suspect this plan will not be the most optimal distribution of experience in the long run. Still, if my calculations are correct, it should get the job done and still leave some semi-decent options for future work afterwards. (The job assignments in Round 7 are something of an ideal, but at that point we can hopefully be more tolerant of less-than-optimal job selection.)
As always, thanks to
fakitap for pulling me down this rabbit hole in the first place, and to
Shuls01 for giving me a good template to start from!