Joel:
First, go to the home page of this forum, go up to the "regional" tab at the top and start clicking. You'll find that there is a regional Speedster Owners Club in Hawaii, so you should have some company in either deciding how you want to go about this or help in building/fabricating/finishing your kit once you get going. Contact some of those folks and develop some new friendships! It's ALWAYS easier doing this with others who've been through it before. There are a LOT of custom cars over there, so it shouldn't be hard to find people experienced people who will want to help.
Second, Yes, it looks intimidating at the beginning, but it is really a lot of simple steps. If you have someone (like your uncle) who can do the welding professionally, then that's probably the hardest part of the whole thing. Even the cutting is easy if you buy a "Sawzall" saw and just take your time. Also, as Slatinsky mentioned, you could get a shortened pan (mostly assembled, too, if you wish) from Kirk at Vintage and then just mount the body on it and the scariest part is done. After that it's all assembly - bolting things together or doing the upholstery work (lots of sprayed adhesive and positioning patience......no big deal). Also, several people on this forum (including me) have heartily endorsed Kirk Duncan and Vintage Speedsters as a fine place to do business.
The Bottom line is, Decide on how much you want to realistically spend, research what's available and what you feel you can honestly accomplish either alone or with friends to help, decide how you want to proceed and then start talking with whomever you want to buy from to get the type of "pre-finished" level, engine, wheels or other parts you'll need for this project to be successful.
Some of us have turn-key cars, some of us have completed cars that others started, and some have done the whole thing "from scratch". There is a wealth of knowlege on this site, and a group of the nicest people on the planet to help you along. Besides, if you put us up for a short stay over there you just might get a bunch of us "tourists" over there to help!!
Good luck, and keep us all involved!
Gordon
The Speedster guy from Rhode Island