I am wondering, ABout how much do you need to upgrade the armor before you get the h-scene with it? Also when does Wil get his new armor at?

its about half way per armour. but ALWAYS at a point where u need a crafted item like fabric toughener I, II, III, IV, V
just exit the enhance armor screen when u get to one of these points and if youve upgraded it enough the heroine should tell you all about how she wants to get messed up in the wilderness

as for wils armour, i forget :3 but i wouldnt bother upgrading his normal one unless ur having troubles (at least i never needed to)

Wil gets his second armor in chapter 7 or 8.

You have to be on the heroine's route and get her 1st H-scene to access her armor scenes. With the exception of gothic ones.

yeah its route specific, you will have to wait till NG+ to see servalwi nakies
however you wont have to upgrade her armor again if you carry over your inventory

Meh i'll be honest the game would have been just fine without the h-scenes, I just call h-scenes a bonus myself.