As far as i can tell for clothing, it seems to be once i got enough clothing changes 5-9 or so (stations with 40+ jobs done), is when it started to bug out. If I can send you my game file somehow, id be more than happy to.
As for rerolling requests it might just be an issue with what I was trying to reroll. I mostly tried to reroll the making out, groping and humiliation requests as it gets kinda tedious when every officer on a station gropes you the same way when looking for a good delivery job. I tried rerolling i think 5 times in a row for one of them and just got the same humiliation request over and over. (maybe blacklisting the rejected request till they promote could "fix" this, have a higher chance of getting what you want if you're willing to waste precious time fishing for it? not sure how well that fits with the spirit of the game)
I would actually be really interested in knowing how requests are weighted and if they have specific requirements to unlock. For instance maybe an officer that wants you to show off your tits is more likely to request you to wear lewder bras or no bra/shirt. Also i've noticed that clothing requests can jump stages and ignore things. Had a station where i went from regular underwear to sheer underwear in a single request, all before i lost my coat. (I'm not saying that's bad, random variety is very nice). I just like figuring out how things work.
looking forward to what those special obligations might be!