Ted,
Wait for the guy. Leave the "little feller" mill in the back with its friend the 4-speed in the meantime. It was good enough until now, it'll be fine for another month and a half.
Once the guy gets to your 5-speed, put the whole shootin' match in as a unit.
Regarding the gearing: go nuts (don't cheap out here). I'd never leave the stock 1-2 main-shaft, unless you plan to be racing Teby for pinks as he suggests-- otherwise, first is utterly useless. I'd go with a longer 1-2 set and keep the rest nice and tight. Stick with the .89/3.88 final drive. Al's right about the highway, but getting a "perfect" highway gear is really, really hard. I had a .82/3.88 with a 2110-- you won't like it. The .89/3.44 is not perfect, but it's close enough for rock-n-roll.
FWIW, 2 months from now it'll be April 9. Most of the rest of us are still bracing for the final snowstorm of the season on April 9.
Just sayin'