Get out your paint brush.....
You want to strip your rudder and your boats bottom of all old paint. Some paints could be compatible and you could add another layer but I would advise against this.West Marine (or competitor) has a brand named product called peel-away. I think it is applied in sheets and you pull off the paint. It is reasonably priced. I have not used it but some friends at www.trailersailor.com swear by it. (check their archives for reviews).Once you get the rudder down to it's base and the boat bottom down to it's gelcoat, I advise using a high quality multi-season ablative bottom paint (see Interlux Micron CSC). It usually lasts me two seasons with my boat on the mooring. Ablative paint wears off as it released bioxides, therefore your days of sanding are over. One you start to see some hull poking thru the bottom paint, add another layer to the thin spots. Different types of paint do not always bond, therefore you can not expect to just cover what you have.Are you keeping your boat in the water? Fresh or Salt? It is best to ask locals who see similar conditions what treatment you should use.Paint on the rudder? I do not do that. I remove my rubber after each sail and put it in the cabin. If you can do this, you should. If it is fixed, then maybe paint it unless you leave the boat on a trailer.Start sanding. Fine paper or possibly a wet sand only. You do not want to dig into the gelcoat because that is your barrier layer. Let your local marine store recommend the process or checkout sailnet.com, westmarine.com, boatus.com for tips.Best of Luck,CraigBoston