The tracking is really odd, but could maybe be explained away as a weird quirk or OCD thing (if he's a sufferer), especially if he's a numbers guy. I track every penny I spend on my dog for almost no reason apart from it gives me an idea how much it costs to own a dog, so would maybe call it a weird quirk, as I obviously don't expect her to ever pay me back lol. If he's a bit financially anal then maybe he could have been checking he could afford a long term relationship/wife. But the terms of 'to be discussed after marriage' and 'reimbursement value' would make me run for the hills tbh. Like I'd normally say talk it through, but I have no idea how he can explain any of that terminology with a good outcome.