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Balaji: There are some kinks with the online shop website that’s being worked on. Maybe check back in a week.
Jesse: First, I think you should go to the local bike partners, Bike Rack and Bicycle Pro Shop for your question. They have excellent staff who are frequently bike aficionado and would know the latest trends and technology and can talk to death to you about bike upgrades. I know, Mark, another co-lead would have a lot of advice for you.
For me, I would first need to know how much you are willing to spend for upgrades. Not knowing that, I would say if drivetrain is functioning smoothly (e.g., derailleurs and cassette), I don’t think it’s good value to upgrade those items individually. The cheapest and most important “upgrade” you can make that will bring significant performance would be to wear tight fitting racing tops/bottom, so there are no folds that will create drag. The next most important upgrade, not cheap, is on saddle and wheels. Since Brooks saddle works for you, I would not upgrade unless you plan on changing your saddles in and out between commuting and training. Not sure what you mean by water post-swim being an issue. I love good wheels and it makes a huge difference for riding comfort and speed. Good entry-level training wheels that you can also use as racing wheels probably cost $700-$1200 for a pair. If you want purely racing wheels, then it’s like $1500+. I don’t really know how much time you would save by buying a good pair of wheels, maybe 2-4 minutes over a 26 mile course? So if you want wheels purely to improve time, I’m not sure it’s worth spending about $1000 just to save 2-4 minutes. My wheels were $950 and I bought them mainly for durability and comfort, because the stock wheels that came with my bike I used for 2 years started breaking apart. The new wheels were a pleasure to ride, it felt more responsive and I knew it would be bombproof and not break over a hard bump or pothole. I don’t know if it improved my speed, but at least I felt faster!
Finally, yes, stripping the rack and fenders on race day would be good to decrease the weight of your bike and reduce drag.