Hey Greg -
Most sails around two-years old will be fine for club racing and getting to know the boat. You probably won't have to rush out and buy anything right away - two seasons is usually only around 20-50 regattas, I'd guess. A reasonably well-maintained two-year-old boat will have you out racing right away.
You can probably just go by age on most sails; on a race boat, jibs are good for about a season and a half before being relegated to "practice sail" status. This is assuming it hasn't been badly flogged in a squall or something. The material should still have a decent finish on it, and it should not be a limp noodle when rolled from the top. The state of the tell-tales might also be an indicator if they haven't been replaced - badly frayed or sun-damaged tells may indicate a jib ready for retirement. Also look for "permanent shape" - if the jib hangs with shape already stretched into it (i.e., the clew is always hooked to one side or the other, bad luff curve, etc.), then expect to have to replace it before a bigger event.
Check for color-uniformity on the spin - I've noticed that coloured spinnaker cloth seems to fade at wear and stress points as it ages. I think there is a fairly wide variation in spinnaker life based upon lofts - some are lasting longer than others. Go over the spin carefully looking for repairs and checking seams - spread it out and really look closely. I think you can get two seasons out of a well-cared-for and well-built spinnaker.
In any case, unless the boat is advertised with newer sails (within the last six or eight months), you might anticipate buying new sails before Nationals in October depending upon your seriousness. I have only experienced new F18 sail purchases from Goodall; a jib and spinnaker were about $1,000 (I think I got a bit of a deal as an existing customer).
Happy shopping - that is half the fun, I think. <img src="http://www.catsailor.com/forums/images/graemlins/wink.gif" alt="" />