Exactly Ladd. My brother recently replayed one of the older pokemon games and told me about how some pokemon came out at night and others during the day. In real life some spots are easier to hit at night time it can't be that hard to do that. And for quick crete and things like that you could easily just have a certain type of obstacle be the type that you can customize.
A flight a stairs + plywood = euro gap/step up....a banked wall or barrier + quick crete = DIY quarter pipe, a hammer + a capped rail = un capped skatable rail.
The same way OG (or S2 I forgot which) had pool draining and un skatestopping it shouldn't be that hard. Hell you could even have it like a spot challenge where if you see something you can skate (pre set by developers) you trigger a cut scene that sets it up to be skatable.
I know you all want BARE BONES GOOD PHYSICS but you forget that at this point we are a cult following. So not everyone thinks the same, we also should make it new and fun.
-peace.