to answer your question about rest until healed my answer is 'no'
with no healing spells or (probably) special abilities your rest until healed times will look ridiculous (although that's not a problem if you can ignore it)
more importantly you should have stolen yourself a ring of regeneration within a few minutes of leaving the first dungeon
you seem to be going along the right lines - don't forget your backstab though - with boots of speed you can stab run and hide round the corner