Great minds think alike I guess, in terms of the shop owner thing! Yeah, TF would absolutely be hard to make, art-wise, even if it's just one stage, from normal to big. But I'm really hopeful there's at least some, it'd work really well in this. Not really sure what you mean with x-ray being harder to implement than full-nude, I wasn't saying that you'd have a movable xray-lens like some games do, it'd just be a thing you unlock. I'm not saying xray as in partial transparency of clothing, if that's what you thought I meant. Visually, it'd be the exact same as "she's nude but thinks she's wearing clothes", just with different background info attached. I also feel like the "emperor's new clothes" thing kinda clashes with the "I'm trying to hide the fact that I'm getting played with/fucked right now since I'm in public".
Clothes compressing body parts is a valid point (although it wouldn't make you have to draw more art, and you could just pretend it's not real, a lot of other games do that.) but I don't see how clothes wetness influences the X-ray mechanic at all (unless you were thinking I meant X-ray as in transparency.)
Picture in picture is a great idea! it would necessitate more art, at least in the case of characters with odd poses (or, just any ass-focused sub-item on a normally-posed character), but I think it's a great way of letting you see every angle of a character, especially the ones like the dragon lady.
Not entirely sure about the timer aspect... having a time limit makes the game feel a lot less sandboxy, and that's kinda one of the original's draws. But, it could definitely work! I just worry that either the timers just wouldn't really matter, or they'd be so short you'd be busy rushing to fulfill the customers' requests to actually appreciate the hotness, but it could be executed well. But, I guess if the final item was infinite time, no holds barred, and that would let you do a more sandboxy thing, then that could work too! Actually, the more I think about it the less of an actual problem it feels like.