Baazinakon

I have a 1999 Schwinn Peleton Pro with the Reynolds 853 frame. The bike has a full Ultegra component set and the frame is seemingly in good condition. The right shifter has begun to not work correctly, as I have to hold the brake lever still while pushing the smaller lever to shift to the smaller rings on the rear cassette. The crank apparently has some play in it as well, however the rest of the components appear to be in decent shape, if anything requiring a tune. I think if I move to a carbon fork the already comfortable frame would only become more comfortable and of course lighter than the aluminum fork that came with the bike (well known shortcoming of the Peleton Pro).

I am doing getting into club rides, perhaps doing a century soon and will be doing a number of charity rides for work. I have also decided that I will train and attempt a triathlon next year as well. I would like to also explore getting into racing the bike as well.

So, to my question. What do I do regarding the bicycle? Should I upgrade the crank, shifter, fork, and wheels? Or should I upgrade the bike and get one of the Kestrels hybrid road/tri bikes? I know one is more expensive than the other but the cost can be somewhat offset by selling the Peleton Pro. the only nine speed shifter I can find is from Bike Nashbar, so I am exploring an upgrade to eleven speed, which means cassette and rear deuraileur too. At this point you are looking at a good bit of money going out for fork, wheels, crank, cassette, shifter, derailleur, etc. I love the bike and it rides great but I am not necessarily sworn to vintage steel. What are your thoughts as to how I should best spend the money given my intended uses?

Thank you in advance.

shelbyfv

If you want new wheels and 11 speed, probably more cost effective to get a new bike unless you plan to do all the work yourself. If you just want to keep it going, you can still get 9 speed bar end shifters. Also, I've read that Campy 11 speed shifters will work with Shimano 9 speed.