That's a frame-specific and possibly rim-specific question. How fat do you want to go? 2.3? Go ahead and try it, if the tire rubs take it back and size down. http://www.sheldonbrown.com/tire_sizing.html
You can go with Chris King if you want to be colorful and trendy, or just get a Cane Creek or FSA if cost is a concern and you're secure with your personal level of coolness.
Alternatives to the Pista - in that price range you have Fuji, Specialized & KHS if they are still making them. A couple hundred more you have Jamis & then at $1k you have Lemond. Around $1200 you can start getting true Keirin & track frames built up to a decent parts kit.
1" headsets - Chris King is the best but to drop $120 on a Pista with a 1" isn't the smartest (in my book - if you plan on riding the bike till it dies do it.) 1" headsets are getting rare and unless you get another 1" bike the resale will be pretty low.
Color - I vote for the green. The chrome ones are ALL over.
The largest tire I ran on my Pista (a 2002) was 28" and that was pretty damn close.
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