Having been to both WDW (multiple times) and DLR (2021) in October, I can tell you we will NEVER go to DLR in October again. The only thing that saved our trip was Oogie Boogie Bash which was a ton of fun. The parks were miserably crowed at DLR in October-- and we have been to WDW between Christmas and New Years and had a great time. I will say that our trip was before Genie + was instituted so there was no fast pass at all-- and it might have been a lot better if there had been some sort of FP. WDW is fine in October, unless you have the bad luck of running into a hurricane (we have). That said, we went to DLR over Labor Day weekend this year and it was great! The Halloween decorations were up so we felt like we did get the Halloween experience, but we did miss the party by a day. If you want to do DLR for Halloween I would shoot for September.
Oogie Boogie Bash tickets can be really hard to get. It can involve sitting at the computer for hours the day they are released, but the party is worth it. We did not go this year, but I heard that passholders got an early access sale (which I hear was a disaster in itself because of the limited tickets and volume of people wanting them), and that left less tickets for the general public which made it even worse to try to get them than the last 2 years. Someone else can probably tell you more about that.
We love DLR and I highly recommend going-- just not in October. People definitely do Disney bound in the parks. I highly recommend park hoppers--- by WDW standards it really is like one big park. Each park does have its own gates, but there is only the width of a football field to walk between the parks- and unlike WDW, you don't pass through security again to go from park to park. It really is 5 minutes to hop. We prefer SNA as an airport because it is a very easy airport and it is only about a 15-20 minute drive to the parks. You can easily taxi or uber from the airport. If you plan to stick to the DLR area, you don't need a car.
As far as food, you can explore the menus and see what appeals to you. In our opinion, DLR has MUCH better counter service food than WDW-- I think because there are so many locals. I could never get by with eating CS the whole trip at WDW, but we could easily do it at DLR. If you are there over a weekend, the Lamplight Lounge Brunch is really good, but it can be hard to get a reservation. If you want a character meal, Minnie's Breakfast at the Plaza Inn is fun- you can usually run at least a character or two you don't see that much at WDW there.