It is really not all that far to any bus stop at either resort so don't think you will have a problem. Hopefully someone who does trades regularly will be able to tell you if you can make specific requests.
Yes and have about as much (or little) chance getting what you want as any member. SSR does not have booking categories so you have no limitations there. OKW has 2 booking categories, near the check in vs otherwise. It's almost a certainty that you'll have a unit that is in the Elsewhere category at OKW but MS will be able to tell you that when you call.