For my $1000, these 4 would be key:
12v sockets and blue sea fuse block on relay: for phone charger, ipod, video camera, etc.
Gotta keep your phone charged for emergencies, plus tunes would be nice
Sargent saddle
Stock seat on my 2003 might as well been a brick
GPS (Garmin Zumo, GPSmap 60CX, or eTrex Vista CX)
Am terribly spoiled by GPS and have it now in both cars, will be my next bike purchase if i keep the vfr
Gen-mar bar risers
Nice for the long straight bits
The risers and the extra sockets are cheep. The GPS and seat will eat most of your coin... but will make a huge difference in the quality of the trip.
Have fun and keep us posted!