1. How important is it to keep your cigars in a humidor?

Doesn't have to be a "humidor per say" could be a tupperware container, cooler, Ammo Can...Anything with a solid seal. Just make sure to clean it well and remove any smells. Throw in a few pieces of spanish cedar to get it smelling nice. For these types of set ups Boveda would probably better than a water pillow

2. Can you rehydrate dried up cigars?

Yes! Although if they are older or have been dried up for a while, the flavors won't be as good.

3. How do you prevent "runners"? Where one side of the cigar burns faster than the other?

In my experience this is usually from construction so there's not much you can do. Smoke slow and be sure to get an even light when you first spark it up.

4. Lacking a real humidor I've been keeping my cigars in a cigar box with a "water bag" (one of those bags with those gel things you let soak in water). I keep the whole thing inside a rather large Ammo can I picked up while deployed. This serves as my "travel case" as well since it pretty near indestructible. I keep a few pipes, some pipe tobacco, and a few other smoking tools in there as well. My question is this...how difficult would it be to convert this ammo can into an actual humidor? And is it ok to keep the pipe tobacco stored in there with the cigars?

http://www.ammodors.com/ <<about that easy lol. Not sure on the pipe tobacco as I'm not a pipe guy!

5. Any of you guys/ladies in western New York? I'm pretty central to Buffal, Olean, and Geneseo.

I'm a Jersey guy

Hope this helps lol