We are also going this Oct to celebrate DLR's 60th
We went for the first time in 2012 (after many trips to WDW) and had a blast! We stayed at HoJo but in a regular room and it was a nice hotel, clean and with a friendly staff just a block or so away from the DLR entrance - a very doable and safe walk. The weather is a bit unpredictable and I have heard that it can be super hot in Oct, but when we went it was pretty cool to chilly. DD tried the pool once but it was too cold even for her (and she will do anything to get in a pool). We are in CO so the cold was not bad at all since it was still warmer than at home!
There are some great places to eat in the area. We loved Mimi's which is right across the street from HoJo on the way to the DLR entrance. We rented a car so were able to go to Target and the supermarket for some snacks, water and soda. We also went to SD for one day on that trip - loved it so much our trip in 2013 was all in SD (I have a mini trip report in my signature).
The first thing you notice is how weird it is to see the monorail while you are off property. Also, Aurora's castle is a lot smaller than Cinderella's - but you can go inside! Really hoping POTC is not down this time, it was down for rehab when we went and I was so bummed! But I was ok once I went on a couple of wild rides with Mr Toad
I had heard that the parks were close, I did not realize how close they really are! No buses, no monorail (although we did take a ride around the park from DtD, we rode infront with the driver which was awesome), just walk across a small plaza.
We did the Halloween party which we had never done at WDW and it was a lot of fun. Tons of candy, tons of characters out and about, no lines to get on the rides, and it was nice to go to the park at night and all decked out for Halloween. Oh and Haunted Mansion decorated with Nightmare Before Christmas stuff is amazing. Another amazing thing - the beignets right next to the HM.
It was a completely different "feel" from WDW - which was good in a way that it did not feel like we were just doing WDW on a different coast