Join Date: Feb 2007
Location: Tariffville, CT
Bikes: Tsunami Bikes
Mentioned: 8 Post(s)
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I'd get an annual.
First it'll commit you to racing, and you may find yourself racing more often, esp since they're sort of "free" once you've paid for the license. I don't think about what I paid for a license in January when it's July.
Second, you get a license
I have a little box of old licenses.
Third, you get some benefits as an annual member. I don't do anything to use those benefits now but I used to (air pass for bike). There's various little things like some kind of health insurance, hotel and rental discounts, etc. Prob no more than a nice credit card but it may be of interest to you.
Fourth, as you pointed out, you can upgrade and get to be a 4 on a current annual license. You do need to do 10 races in a year so the annual will be cost effective if you decide to go for it. As a 4 you get bigger races, more variety (Masters etc), usually longer races.
Fifth, since one day license fees do not carry over to annual fees (i.e. if you did a One Day this week and bought an Annual next week, you don't get to discount $10 off your annual), if you want to do more than 6 races a year, the annual is the way to start off.
I would do One Day only if you know you don't want to race regularly (1-3 times a year, no 'cross or other off season racing) or if you've never tried racing before.
Disclaimer: I am a volunteer for USA Cycling as the CT state rep and I also promote races under USA Cycling auspices.