Re: How do you optimize your upwind performance?
I do a combination of things, but mainly looking at the genoa telltales and the mainsail shape, and looking at the wind indicator. One useful trick on my boat is to put the autopilot on, and trim the sails so that the rudder is amidships, on the principle that a balanced boat sails best. That usually means having to bear away little as it is difficult to achieve good balance if pinched up too much, and results in more speed.
On my boat the bimini makes it hard to see the masthead indicator without leaning back a long way, but I do it from time to time.
On my recent trip to Turkey I think about 75% of my sailing was upwind.
Comparison with other boats where I sail does not work very often as so many of them are charter yachts, frequently with inexperienced skippers, and generally with poor sails, e.g. baggy old genoa and in mast main, and simply do not point as high as my boat with a (smaller than standard) tri radial genoa and a new fully battened main.
Working on immortality - One day at a time.