Ryan,
Ahh, another America owner with buyer's remorse(just nad bustin').

If you had a Speedmaster with those dual front brakes, then you wouldn't have as much problem stopping.

You're right though about looking at the entire bike when doing performance mods. Suspension, brakes, clutch all need to be factored in. And the stock carbs aren't going to do you too much good when pumping up that motor to 1100cc. That's the first thing you should do when starting a project like this...sit down and make a list of all the costs. Talk to Bill or whoever and go through what's going to be needed for parts and other costs.
So far for the 1100cc kit, I have the following costs from the Delphi forum. However, some of the costs may vary:
1100cc Wiseco kit: $885
Jojje billet head: ~$500
Powdercoat head: $100?
Carillo rods: $700
Bore and sleeving head: $250-300
Case boring: $250
Gaskets: $82
There is no cost posted yet on dynamically balancing the crankshaft. I think Bill guesstimated that it would run $300-450. There are other costs not listed, like Triumph seals, o-rings, stronger clutch springs, and what not. For floating rotors and stainless brake lines, check Brent's site.