1. Bentley lists .315 to .316 as the spec for new guides. No wear limit is listed that I can see, though.
2. Yes, if you have (access to) a hydraulic press. Not sure how many tons you need, though, probably a lot. You can also test for guide wear by putting a valve in and seeing how much it rocks side to side. Wear limit is .051 for exhaust and .039 for intake valves.
3. Dunno.
4. I plan to have the ports polished on a spare head I have. I'm not planning on porting it though. VW diesel heads are famous for developing cracks between valves, and I'm afraid that removing any more material will lead to catastrophic failure. I don't know that much about it though, maybe you could just remove material from the manifold end of the port and be fine.
People have put diesels in Vanagons which are pretty heavy (and have a lot of wind resistance). Engines tend to last only 100,000mi in this heavy-duty usage though. How much HP depends on how much $$, really. Turbocharging up to 30psi is possible, and with the fuelling mods to go with it you can get 100-150HP or more.