Quest...glad you dropped by....
And we don't mind a little buttering up, especially from someone who appreciates the theme and atmosphere of Wilderness Lodge and the villas!
I can take a poke at your questions...
You've already looked this up, but studios during the peak DVC seasons are challenging at many resorts. I can't speak directly to studios since I book 1BRs, but in general I think that if you are online and ready to hit the "book it" button right at 8:00 am Eastern Time you have a good chance. VWL is one of the smallest (fewest villas) DVC resorts so you don't want to miss that window! I think a lot of people still call MS to book reservations and they don't open until 9:00 am so the chances are that they will have a very hard time booking a studio during peak times.
Of course, you could walk the reservation but for me that's a lot of work, especially since I've never been shut out at the 11 month window. But again, I book 1BR villas so I am booking a much easier category to obtain.
We haven't had a car for many years now at WDW. Lots of our table service meals are in the parks so we just plan to visit that park that day with some FPs around the time of the meal.
If we are going resort-to-resort for a meal, we tend to take the leisurely route from WL to a park, then a bus from that park to the destination resort. For example, if we have an ADR at Boatwright's at Port Orleans, we might take a bus to EPCOT and then wait for the bus there to Port Orleans. Or if we have a reservation at the Grand Floridian Cafe, we just boat over to MK and then take the monorail around to GF (or walk to GF when they finish the walking path!).
We are rarely in a rush mode at WDW, so the transportation transfer system works fine for us. At most, it takes us about an hour to get from WL to the other resort...generally it is much less than that. On the rare occasion that we are running late to an ADR, we use Uber or Lyft to get us there.
I don't think this is a different situation than SSR or any other resort. The difference at SSR is that you can walk to the Disney Springs bus stop and board another resort bus so you don't have two buses to get there. Sometimes you can get creative: ie. take a boat from WL to Contemporary or Fort Wilderness, or take a bus from WL to DHS and walk to the Boardwalk/Beach Club restaurants. But it isn't a lot different than staying at other DVC resorts.
Good luck with your VWL resale. It is a great resort and I'm sure you will love staying there as an owner. Let us know how your resale search progresses!