I just found #2. The game is called 3D Dudes. The developer seems to have dropped off of the face of the planet, and all internet downloads seem to be only the shareware version. Although according to most sources, that's for the best since this apparently was an absolutely atrocious game. Still, I remember it from my childhood and it makes me sad that I can't dig up the full version... Or run it with Vista.
#1... I don't know. It COULD be
Wraith I'm thinking of. But... Even after playing the shareware I'm not absolutely certain. How stupid is that? I can remember playing a game, but I don't even know if this is the same one. Maybe I made the game up. I don't know, this SEEMS to have similar gameplay and a similar inventory system... And the character creation seems familiar (then again, I played pretty much every one of the games on these "1000+ Great Games!" CDs, so a lot of stuff is familiar), but I could've sworn that the game I'm thinking of has larger sprites for characters and is a top-down view, not this pseudo-3D stuff. I also remember it being more... Cave-like. And fighting some kind of green enemy, though I can't remember if it was a lizard, an orc, or something else entirely. I'll try to find a full version of this and play it a bit more, but in the meantime feel free to make more suggestions.
Also, thanks for the previous guesses guys.