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Yeah, I think the rule would have to be that it just doesn't work. So don't buy with PP anything you hope to sell later.
If it could be sold, you would presumably make back half of the upgrade cost, and none of the "purchase" price. But implementing that rule would be a pain and would make auditing a pain and is just the sort of problematic type of thing that I imagine the campaign staff is likely to handwave and say, "nope."