will let the experts discuss the longboard, GO, START, RIO, etc
my concern is the shoulder
i broke my shoulder doing windsurfing on ice
this happened in march about 2 years ago and i only missed about 3 windsurf sessions that spring.
so, for you - do NOT attempt to windsurf on ice OR snow
on the other hand, when progressing one does tend to catapault frequently and hard at times
however, i have rarely , if ever landed on my shoulder
for uphauling - you can stay with smaller or lighter sails , use an EZuphaul or learn to beach and waterstart
as you have said - there will always be risks, but i do not see it as a serious hindrance !!!
in terms of your equipment - others will ask what have you done in terms of windsurfing up to now ie ever ?? harness, gybes, planing, etc
lotsa luck buddy !!