I can tell you what I use, whether its the best, that I can't say.
First thing don't skimp on the sunglasses. In parts of the Caribbean they're the only good way of seeing water depth and underwater obstacles before your do yourself some damage. Also get some sort of lanyard to attach them to yourself.
As long as I've been sailing (and that dates from the time of the plesiosaurus) I've been wearing Sperry Topsiders may not be the best but they're comfortable and have never let me down. Instead of dock shoes and sailing shoes just get two pair of sailing shoes. FYI it's a small boat, tyour feet tend to get wet.
1) whatever you get, make sure it's 'breathable'. Truly waterproof gear is generally to hot to wear. Best bet to to wait for sales cause good .stuff is generally expensive. My wife got a really nice Henri Lloyd offshore jacket and bib pants for about half what I paid for mine.
2) now that I've stopped racing, glove tend to last for a long time.
3) never worried about that, cotton does me just fine and expect it's a lot cheaper
4-5) see above
6) make sure you get a light-weight hat with a nice wide brim. Baseball caps don't do it for your neck. and as I said get good sunglasses -- not high-style --. The will set you back at least $80 but on the water you need to protect your eyes and still have good vision. My wife has rose tinted Maui Jim's which she really likes. I have regular Harkens. There are better, so I'm told, but not significantly and they also cost a lot more .
BTW I have no financial interest in any of the companies I mentioned and I expect there are other brands that are just as good