CHR starts to diminish in its returns after about 110 total CHR. There's a great discussion on the lolalla bard forums which have to actually be the best discussion forums for bards I've found, lots of good people post there, especially Vilurum who has gone out and done a lot of testing of stuff such as CHR return, string/wind skill etc. String seems to be natively weaker than wind regardless of skill level. I only use it for Horde Lullaby, Paeon and attempts at Threnodies with the appropriate instruments (if I get resists on threnodies I'll swap out for wind though).
http://ffxi.allakhazam.com/db/jobs.html ... 5357358707 is a good discussion of singing vs wind. Good ways to skill up string are besieged, in sea on dolphins, or macro'd in for Finale which hardly ever resists which is how I did it (before I got sea or ToAU came out).
As for endgame gear, I have a "general" setup which I do most things with which is mostly a skill build that keeps CHR at around 110. This includes Tamas/Angel ring, Musical earring/Melody +1, Miraculous cape, Gleeman's belt, Osode or AF+1 body, AF+1 hands & legs/AF2 legs, AF2 feet and hat, string/wind torques. This is a pretty reliable setup I can debuff most HNMs and stuff with (247 wind skill, 243 singing with one merit in each), and is also pretty much what I pull in for meriting. I also have a MP build (swap out earrings and rings mostly and add in a couple of things from my WHM like Steppe Rope) which is useful for dynamis and things like that, and a couple of other builds which I don't tend to pull out very often, such as my dynamis pulling gear (HP, evasion, powder boots, etc. lol), etc.
Food, well, I use tacos almost exclusively.
To spice up my endgame bard life I've taken on a bit of pulling in dynamis, lvl'd my WHM up and insist on going as that on occasion (fortunately we have quite a few other-job bards so that's not too hard) or try to wangle myself into a melee party as much as I can heh ^^;
Bard is fun, relax and enjoy it ^^/
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