Wow, I never imagined when I was eating my lunch at work today and starting this thread based on an off the cuff conversation that this kind of insight would be laid out. Thanks to everyone that has posted so far. I think anyone working on or starting a project would be well served to read through what all you guys have had to say.
Personally, I am trying to stay focused because the project I am working on is my Dad's. He has trusted me to bring his dream vehicle to reality. He has work multiple jobs (construction) all his life to provide for our family. He has let me do whatever I wanted. I've raced go-karts, rode atv's, he put me through college, we built my 69 Camaro in High School, we raced stock cars and now it is his turn. That's why it is important to me to actually get to the end of this project.
Other than changing engine choices (which he was fully in favor of) we have tried to avoid alot of these pit falls. We try to plan steps ahead so that we know where the expenses are and what we have to spend each step.
We also try not to buy then re-buy. For example we almost fell into the "Bigger Brake" pit. We have 13" 6 piston Wilwoods for the front and 12" 4 Piston for the rear. Then they came out with the 14" stuff. Do we NEED 14" 6 piston mono-blocks all the way around for what he wants to do with the truck. NOPE! Were they new, trick, and twice the price YES! That extra 14-1500 will be used very well someplace else.
Even trying to be smart, this stuff is still expensive.
In the end, no matter what it turns out like I would never trade the time my Dad and I are spending together working on this truck. The new friends that I have met along the way from this site and other places are just bonuses! It's not just about the cars.