wingkng,
There's no guarantee that the Comedy Warehouse and Adventurers' Club will always be there. The Internet rumor is that the Raglan Road Irish Pub, which replaced the Pleasure Island Jazz Company, marks the beginning of what will be a transformation of Pleasure Island from unique, Disney-operated clubs to leased restaurants operated by outside companies.
wingkng,
When Disney sees the opportunity to make money with a table-service restaurant at SSR (either by operating such a restaurant or by collecting rent), there will be a table-service restaurant. Keep in mind that restaurants and shops at
DVC resorts are not part of the "condominium," but are operations through which Disney makes a profit or takes a loss.
The theater at SSR is similar matter. The theater is also not part of the "condominium." So the question is, what kind of live events and concerts could Disney profitably run for a limited audience within the gated resort (even by opening the events to non-SSR guests)? Or are you suggesting that the events should be paid for by the SSR members' operating budget in other words, by an increase in your annual dues?
Retail space falls in the same category as restaurants. Disney resorts each have some sort of combination souvenir and convenience store, but the main shopping for Disney guests is in the parks and at Downtown Disney. I wouldn't expect that to be any different at SSR.
Enjoy SSR. It's a lovely place. But don't count on seeing "SSR mature into a more 'high-end' resort," as you define it.