Pepper was kind of my experiment in a character that wouldn't respond well to MC's attempt to insert himself into her life, and she'll continue to be a little stand-offish for a while.
But, stay tuned for more on this. MC might learn that with one of the girls, indulging her every whim only serves to spoil her, not make her better.
We saw him begin with something like 26 million. It's far from infinite money, but for someone who's mostly cutting checks for 10, 20, 30 thousand? Eh. Even assuming he wasn't earning interest, he had no stocks, no money-making investments, etc. he could drop 50,000 per month, for the next forty years, before he ran out of money. He's gonna be juuuuuust fine.
In all likelihood, that'll be more like endgame content, and vary from girl to girl. Like, Corrupt Pepper could decide it's worth it to hang around, and keep her allowance from MC while she pursues writing. As long as he's not a dick, getting dicked down by a millionaire is probably better than waiting tables. Nicki's likely in it for the long haul. Ashe will probably break away as soon as her position is secure enough she doesn't need MC. MC and Gabby's sugarbaby relationship can be assumed to end whenever she leaves for college, which will likely be at the very end of the game.
Honestly, I wouldn't want to block any of the main love interests from nice guy/corruption routes, but some of the secondary girls will vary a bit. I think I've already mentioned this, but I have a little Bonnie scene planned for the event that the player is solely on Ashe's friendship path. And Tessa, Jamie's friend who helped him 'shark' Gabby and Brittani, will likely require some special attention.