I'm not exactly certain what that dealership is selling you for $250. Harley no longer sells the old Stage I Race calibrations that used to cost around $150, since they are illegal. Any legal downloads they have these days are for the EPA approved kits they sell, like big bore kits, higher flow air cleaners, etc., and those don't affect the operating range of the bike that's covered by the emission regs. In other words, you still have the closed loop engine management system controlling the fuel mixture at the legal settings for most normal riding conditions, and the only thing that changes with a download is the mixture for higher throttle and load conditions, like hard acceleration. If you really aren't changing the amount of air flowing through the engine, those downloads just make the bike run too rich in open loop mode. Are you actually having a stage kit installed, or just having a download installed? IMHO, if you aren't changing the exhaust and intake to allow more flow, the download is a waste of money. You'd be much better off to have the bike properly tuned by a fully competent pro. It will cost more, but at least you'll get something that is right for how your bike is actually set up.
Btw, a CVO is already considered Stage I right out of the crate, since they come stock with higher flow air cleaners and mufflers compared to regular production models.
Jerry