Well, you're asking in the offsite housing boards...so I think we're all biased towards staying offsite here, but honestly, it's usually a lot cheaper in my opinion, especially if you eat some of your meals at home.
If you book a WDW Resort the big "extra" would be use of their transportation I guess. You can use the Disney Magical Express bus to get to the hotel, then the Disney bus system to get around WDW. Of course, now you're locked into eating every single meal somewhere on the WDW properties. Personally, I hate taking buses when I'm home, and I'm not about to go on vacation and wait for buses and stuff... I'm renting a car! (priceline.com...under $25/day in October). Oh...one thing if you have a car though... you have to pay $10 to park at the parks each day.
Now, to be fair, there are other perks like Extra Magic Park hours, the
Disney Dining plan, etc, but you're not going to end up in a place that even comes close to being as nice as you can get a vacation rental home for way less than staying in a value resort typically, and then you don't have a kitchen.
Personally, I think October is one of the VERY best months to visit WDW...weather is just perfect, hurricane season is basically over, not too hot, crowds are relatively lower than normal, prices are not at their highest (so you should be able to get a great deal on housing still, but need to start looking now to get the best place and best deals!).
You sound very budget conscious or oriented, so I would imagine you would be looking at a POP type value resort, but for less $$ per night you could be in a beautiful 2-3 bedroom condo in a 5 star resort setting that would blow away almost ANY WDW hotel room, but then you have to have a car, if you were going to be driving down or getting a car anyways then the decision is easier.
Personally I love Windsor Hills Resort, there are also other very nice resorts in the area, someone mentioned Cypress Point, other popular options amongst helpful advice you will get here on the DIS include buying someone else's DVC club points, or other area resorts directly from the owner, or services like skyauction.com.
Here's a map of the area resorts I've found to be excellent!
http://www.thedibb.co.uk/villa/map.htm