I''d have to say the primary pieces of information are 1) do you know how much you like racing and 2) how deep are your pockets?
Initially, if you haven''t raced I''d say race it with what you have to make sure you like it. Doing cruising canvas class, no spinnakers. With a boat not prepped, you will probably get creamed (we did), but with the right attitude you will still have a good time and learn a lot. Then decide whether your current boat is adequate, or if you need to move up/over to something for racing oriented. My story is similar to yours (see below).
What are you thinking of for mods to the boat? To get that boat racing to it''s PHRF rating (around 195-200) at a minimum you will most likely need to shell out for some sails, an perhaps some bottom work. If you are planning on racing spinnaker then that''s potentially another set of issues (more sails, hardware, etc.)
Depending on what you do and how you do it, your improvements may not help you on resale should you decide to move to a different boat.
Another thing to consider - even with a boat in optimal shape your crew is a big factor. With a newbie crew, it doesn''t matter too much what you spend. Save your money until they start learning.
Two years ago I purchased a C&C 37 with a centerboard. She had so-so sails and a soft bottom paint with a texture like the surface of the moon. I figured I would use her for coastal cruising and around the cans on Wednesdays at our club. What I didn''t count on was how much I would like the racing.
We raced the first year dragging a shag rug below us, and using a delaminating, blown out head-sail that dropped chunks of Mylar on us during the races. We got clobbered every week, and had a blast. Won the Port Tack award for the club too; free racing for 2001!
For 2001 I completely stripped the bottom and repainted with a hard paint. Also we built two new sails. It was like having a completely different boat. We didn''t start winning, but we started occasionally beating other boats. We noticed that when we were last, we were last by 30 seconds instead of 30 minutes. At this juncture we''d basically eliminated the boat as a factor, now it was down to crew skill. I probably spent about 10-11K getting to this point, however.
At the end of this year I convinced my wife to move to a Beneteau First 40.7; both for the racing performance and the cruising capabilities. I''m psyched for the new boat, but kicking myself in the butt over the money I dropped on the C&C as well. But then, if I hadn''t learned on the C&C I wouldn''t have wanted to make the move to the faster boat, so I could go around on that circular logic forever. I will say that in trying to sell the C&C, I''d rather I had a cruising bottom on it right now.
So, IMHO I would say try it and make sure you like it, then evaluate how serious you really want to get about it. One thing I''ve seen is that it''s a pretty addictive sport. If you like it and can afford to do it you can go pretty overboard with the spending.