What should I look for in my first 60-66 truck?

[Quickly Addicted]

First off, I'm new to the boards here. My name is Chris and I recently moved from CA to a northern suburb of Dallas, TX. I've been reading the posts in here for a few days and I'm impressed with the wealth of knowledge (and work ethic!) on here. I'm sure you guys can point me in the right direction and help me make the best choice.

I'm going to be needing a truck here before the end of the summer, and I think I'd like to get an old 60-66 chevy. I'm going to have about 1000-2000 dollars to spend. I need something that I can drive nearly everyday, so it pretty much has to be in decent driving shape to start with.

Also, I cant afford a money pit. After buying this, it's not likely that I'll be able to sink a lot of extra money into it.

I'll be buying this as something that I can work on occasionally, I'm never going to do one of the gorgeous frame-off restorations that I see here. I just need to get around and haul stuff home to fix up a house. While driving a great piece of american iron.

So my questions are:

1. What engine is "best"? Does an I6 get any better mileage than a small V8? What about reliability/strength? Do the I6's wheeze like I do running up hills lol?

2. What year is "best"? Loaded question I know, but does one year have any features that make driving them more comfortable or easier?

3. Should I look for one that has been converted to 5 lug wheels and power brakes and steering? I'd prefer something easier to work on and less likely to leak so I'm thinking that all orig would be better, but I i dont know much about these so correct me if I'm wrong.

4. How wide are the beds of step sides and fleet sides? I need to be able to put a full sheet of plywood or sheetrock in it at home depot. I do plan on using it as a truck for awhile at least.

5. Is there a "best" transmission? I dont care for 3 on the tree, but I'm leery of getting some hacked up conversion to a floor shifter. I'm thinking that an auto would be better for me, but again, correct me if I'm wrong.

In general, what should I try to find or try to avoid? Thanks guys. BTW, you've got some amazing looking trucks on here.