<< I'll trade some performance for reliability and ease of work.>>
I think you'll find a properly tuned 2 barrel or a single will be equally reliable. The single is a really easy fit though, so if you're going to buy a new one, I'd go for that. it's just a bit less power. Put the 2 barrel on ebay and you can cut your cost.
If you're looking for reliability, you'll ultimately find that the stock stuff is fine as long as it's cleaned an properly tuned. That's with the exception of the carb - the weber is probably the way to go due to cost. If memory serves, it's less than a stock one.
If you order points/condenser, new fuel lines and filter (get a few filters since they are cheap and if the tank isn't new, it's probably got some crap in it), wires, plugs, etc., you'll go a long way to getting it running pretty well.
Another thing to check is all the wire connections. I've had grounds go bad overnight for some reason. If your truck has been 'modified', the wiring is likely a little messy. Cleaning the battery and starter connections tends to make a big difference.
Have fun.
Mark