Jay,

I think the level of support is country dependent. Some countries are putting tons of money into their national sailing programs- Singapore is a great example. Team GBR relies on national lottery funding to help support its sailors.

I think the US got caught behind the curve when it came to national team funding and a very professionalized program. For a long time we dominated Olympic sailing using a very individualistic model... so we didn't change that model until all of a sudden we were playing catch up (at least IMHO). The good news is the US Sailing Team funding to athletes is increasing, hopefully reducing the individual burden slightly.

The simplest answer to the collegiate question is that the current college system works really well by some measures, and is difficult to change.

Not sure why USS membership doesn't go towards Olympic sailing, although I know many wouldn't support it.