So I'm going to be pulling my Holley 2B carb tomorrow and rebuild it. I have never rebuilt one and am looking for any tips or advice heading into it. I have the Holley rebuild kit that has some directions but could use any additional advice.

How long should I soak pieces in carb cleaner? I'm also nervous about re calibrating it after I rebuild it.

Thanks-
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Depending on the amount of varnish/crap on them, I usually let them set for 30 minutes or so. Usually long enough to finish cleaning up the top of the intake manifold, checking my fuel lines and vacuum caps, etc. Then each piece will get all little longer soaking time in the can while you work your way through the soup in there. I'd start with the small pieces first. Gives the bigger chunks more soaking time.

For now, just concentrate on getting it put back together correctly. That's the challenge. There are plenty of how to guides out there on the ol' interwebs to talk you through dialing it back in once reinstalled. I just haven't touched a Holley in so long I can't lend advice on that side of it.

Just personal experience here with Holleys, but spend the money to have someone do it for you if you aren't familiar with a carb rebuild. Holleys are extremely touchy and if they aren't set up right, they will give you nothing but trouble. I had a 2B on mine for about 7 years then swapped back to the FoMoCo. Then I went EFI and looking back, I wish I never had it. I had it professionally rebuilt 2x to be tuned for both off road & high elevation and it never ran well unless it was on the highway running 50+ mph. I have rebuilt several carbs before, Quadrajets, Motorcrafts, Edlebrocks and even a single barrel Willys carb, the worst to dial in was that damn Holley. If you do want to do it yourself, read several articles on it and do your homework. My opinion of Holleys isn't very high on a 4wd vehicle, on a car, I'd take one without hesitation. Just my .02 so take it with a grain of salt.

I love my Holley 4bbl on and off road but absolutely hated both edelbrocks I've had in an offroad setting, to each his own I guess. But i would have to agree with Gary if you don't know Holleys you should have someone else do it, if you're interested I have a good running motorcraft 2bbl I just pulled off of a bronco I'm restoring

A trick I use is the gasket between the Carb and intake smear a thin layer of grease on that gasket. Both sides. It helps seal that spot and allows you to remove the Carb later without having to replace that gasket.

So I am not having any "issues" with my carb but just thought it ought to be something I should do since it had sat for a long time. I was told rebuilding a carb was not that difficult which is why I thought I could tackle this myself.

However-- if Holleys are that touchy, I may decide to take it to someone to have it done. Does anyone have any suggestions on places to take it? Any general idea of what it should cost to have it done?

Holleys arent any more touchy than any other carb. The only thing i hate about them is the stock metering block and bowl gaskets. They stick like no other. A can of aerosol gasket remover simplifies that, though. If it ran well, and you just wanna freshen it up; do it yourself! They're easy. Soak the parts, or just attack the orifices with a can of carb clean and compressed air.
I figure by doing it yourself successfully, you gain the knowledge and confidence to tinker with it if/when it gives ya problems down the road.