Join Date: Jan 2004
Location: Fremont, CA
Bikes: Ti Sports roadie, Cannondale CAAD 3, Tern Cargo Node, Helix (soon)
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Rim tape lasts forever, provided you don't have sharp spokes or burrs constantly rubbing again it (rare) - that's why I'd do a quick sanding first just to make sure. Rub a finger around the rim; anything sharp or bumpy just file/sand/rub down. Other than that, the only time you may need to remove the tape is if you're replacing a spoke or something.
The only other thing is to buy the right sized width tape. For a 305 rim, you'll have plenty of tape left over. Maybe you'll be able to use one roll for two wheels. No guarantee though.