Are you a one bike guy or a multi-bike guy?
If the former, then I'd slow down and start researching the perfect do-it-all-for-Barry bike. It IS out there. Currently, there are more American indy bike makers than ever before, making well built designs for all kinds of needs. Consider this a 6-9 month endeavor.
If you are a multi-bike guy (I sure am!) then buy a go-fast bike for fun and also modify your Trek's gearing. The operating limits set by Shimano, et.al. for their derailleurs is always very conservative. My Kogswell goes from a high of 104 gear inches to a low of 21gi with only 2 chainrings (middle and inner). You could conceivably put a larger ring on there and go to 120gi. HOWEVER, you'd have to realize that dumb cross shifting (big ring to big cog) will royally screw up your drive chain, but no thoughtful biker would shift that way. Consider a 53-42-28 in front and a 9-speed 11-34 cassette. Then forgo all thoughts of index shifting for the front derailleur (personally, I think they suck anyway). Indexing will work fine on the RD, but you'll need to be able to make small adjustments in the FD.
I can help you work it out if you need any help. -GB