We are going to be staying 11/14/20 to 11/19/20.
If you are not going until November, DVC availability for Boardwalk owners only *just* opened up. Its still very early for any of the DVC rental brokers to have any availability. It just means that the brokers have no Boardwalk owners with enough points to accommodate you at this point, it doesn't mean the resort is sold out of 2BR units. At the 7 month mark, any DVC owner can rent their points (not just Boardwalk owners), so it becomes much easier for the point brokers to have enough availability of points. If I were you, I'd check more than one broker and get myself on the wait list, so that if a Boardwalk owner happens to come through, you have that pending request for points.
That said, your dates may coincide with Food & Wine, and Fall is a very busy time for DVC in general. Its possible they may book up prior to the 7 month mark because of this, so definitely have a backup plan.
Pros/cons to multiple rooms vs 2 bedroom.
If you decide to book through Disney and book multiple rooms, IMO the pro is that people have their own space. I'm not sure what the ages of your group are but if you're traveling with extended family, I can speak from experience that its nice to have your own space to retreat to at the end of the day. If you're one immediate family of 6, keep in mind that they will not guarantee you connecting rooms or even rooms next door. They will try to accommodate the request, but its possible you could be down the hall or a floor up. If there's only two adults, you may need to split up in that case.
What parks are closest to the parks? I would love to be within walking distance of one or two.
I assume you mean which resorts are closest to the parks. Yacht Club/Beach Club and Boardwalk are in walking distance of Epcot and Hollywood Studios. Contemporary is in walking distance of Magic Kingdom. For all of the other on-site resorts, you'd have to either take a bus, boat, monorail, or gondola to the parks. Animal Kingdom is only accessible by bus (unless you're driving yourself, of course).
Swan/Dolphin resort is also in walking distance of Epcot and Hollywood Studios; however, they are not considered true Disney resorts. They are owned and operated by Starwood. Their location is great, and often their price is great too. They have many of the same benefits as an on-site resort, but there's some key ones that are not included. For example, they do not come with complimentary Magic Bands, you can't get a dining plan, and no Magical Express from the airport. There may be others I'm forgetting.
We would love a really good bar at the resort that my husband and I can relax at after getting everyone settled in for the night.
The Epcot resort area (Yacht/Beach, Boardwalk, Swan/Dolphin) is probably best for this because each has a lounge, but its easy to walk to the other resorts as well for more options. Boardwalk also has ESPN Club, Jellyrolls, and Big River Grille which would be good for a night cap. Swan/Dolphin also caters to convention attendees and business travelers, so their lounges/restaurants usually get good reviews because of this.