Here's my 2ps worth but I'm no expert...
1. I would let him cry for about five minutes. Doesn't sound like a long time but when a baby's crying it can seem like an eternity lol! Five mins is a perfect time for my DD as if she goes past this point and is still crying, I know for certain that she'll need help.
2. I don't know about the length of naps - I've always been of the belief that a baby will take the sleep they need unless OT. I'd try not pt/sh-ing an see how you get on - it may be that he's actually able to settle himself back off...?
3. I *personally* would let nature take it's course. I doubt very much that his NW'ings are down to hunger.
Is he quieting down as soon as you enter the room? This could be SA (although he seems a little young).
Hugs honey. I know this can be so confusing and sure as Hell I'll be on here in a few weeks (lets hope not before
) at the end of my rope needing answers!
Take care and let us know how you get on!