This has only affected Pete for me, but his remaining quests aren't decreasing. I've been sitting at 5 of 3+2 quests remaining for a good 10 quests now. Did other quests as I go left to right and still had a bunch left, and returned to Pete with same effect.

No, if I remember correctly, this seemed to resolve itself about a week or so after I first posted this. I feel like I'd have way more money if it hadn't as I did to some extent just keep doing his quests more than I should have been able to.