Ive been through that same cycle (no pun inteded) over and over again, more times than you could imagine. I have built up, from the ground, 10-15 bikes. I think its always best to buy the best quality you can afford up front. Also, education as to your needs and potential use goes a long way into making the right decision.

People change, needs change and like anything else a bike is a constantly evolving machine to suits a evolving lifestyle. There are no absolutes.

Dont think of your costs as 'losing' money, everybody goes through it and it is really the only way to learn what works and what doesnt. Cost of experience!

I have a LHT with custom spec'd components. I didn't use top notch stuff, but affordable at the time and higher quality than what the LHT came with stock. Overall it cost me $500-$600 more than a stock LHT build. My plan is to eventually replace the frame with a custom spec frame down the road.

The process of researching and ordering all the components is very enjoyable, I love it more every time I do it. I would suggest getting a good frame your comfortable with, spending a couple months here on BF, setting up a spreadsheet with costs/components options and figuring out what works for your budget. It is alot of fun!