Fiberglass tanks are pretty inexpensive. You can get them for about $60 for the 17 lb. size.
Winches—it might be worth looking on eBay or waiting for the Defender spring sale.
Halyards and running rigging, call up R&W Warehouse in New Bedford, MA.... great prices, good people.
LRSE is the place to send the liferaft. If you can attend the repacking, I'd highly recommend doing so. They're in RI IIRC.
I like the Garmin 18 HD radar and think it is better than the Furuno, and you could get the display as your new GPS—killing two birds with one stone so to speak.
The Icom M504 is a good unit and allows you a remote command mic. Has full DSC support with NMEA out and in. Standard Horizon just came out with one that has a limited AIS display and provides AIS data. This would probably be a nice feature to add if travelling in areas with heavy commercial shipping. Don't remember but believe it can take a remote mic as well.
A saltwater washdown pump is a great idea... I'd recommend one both in the cockpit and one in the anchor locker. To reduce the number of through-hulls, it might make sense to combine the watermaker intake and the two wash down pump intakes in a single through-hull with a sea-water manifold.
Instead of taking Red Cross first aid and CPR courses, I would highly recommend taking a more advanced Wilderness EMT type first aid course. The Red Cross courses tend to focus on first aid where good medical help is relatively accessible. If you're out cruising, that won't be the case. The Wilderness EMT type courses tend to focus on the skills that are needed when medical help is hours to days away, rather than minutes.
A watermaker is good for several reasons: First, having a watermaker allows you to be more self-sufficient... the longer you can stay away from marinas, the better off you are. Second, some places have either no water, expensive water or bad water... and if you have a watermaker, passing through these areas is easier.
Try and size one so that you don't have to use it everyday, but every third or fourth day. You'll probably want to install a separate tank for the RO water, so that you can check the quality and so that you can keep it separated from the shore-supplied water, which is often chlorine treated, since chlorine will destroy the RO membrane and you need RO water to backflush the membrane when shutting the watermaker down.
The wind gen you're probably thinking of is the DuoGen unit. It is regarded fairly well and the water generator is good for long passages, though it will cost you some boatspeed.
Hope that helps.