I have a friend who's looking to buy his first firearm.   He's looking for something bolt action and while he's not picky about caliber, I figured no better place to start then .22LR.  Does anyone have any recommendations about the various bolt action .22s?

CZ 452 or 453. Savage MKII is good too.

I have a Ruger 77/17 that I bought a .22lr barrel for, and she's a very well-built gun. Usually up there in price, but keep an eye out for places like OGC-- I got mine there for under $250. They take the same magazines as the 10/22, and are far better built than the bolt-action Mossbergs Sports Authority has from time to time. It's a gun I would recommend buying if he's the type to spend a little extra now for something he wants to hold on to. As for the CZ, my cousin has their lower-end 452, but it's still a fine gun. Trigger could use a bit of work though, very rough. The higher-end CZs are beautiful.

You won't go wrong with a Savage.  All of their .22 rifles are excellent in terms of price/performance ratio.  And, they are one of the few manufacturers out there who make left-handed bolt actions.  They definitely have a model in your price range (whatever that price range is.  They have a LOT of models and options).

Stalk the local gun shops, and look for a Mossberg in the M44 family.  Excellent guns with excellent sights.

Also, take a look at the CMP. 
http://thecmp.org/Sales/rifles.htm
They have both surplus and new .22 target rifles.  These are guns for people who are serious about their .22 accuracy

I have been using a Savage MKII BV. Great value and very accurate with the right ammo.
I use it for cheap practice for long-range wind reading, shooting it at 100 yards with a scope. It is possible to land 10 rounds of Wolf Match Target inside of an inch, as long as I read the gusts and letoffs correcty.

I am working on mounting some aperture sights right now. Change it up a little. Hehe.