The last few trips I have thought were the last hurrah before having kids, but I haven't felt compelled to go down that road yet, if at all!
We just did WDW at the end of September. I think Food and Wine started mid-month. It was a nice addition to our trip an we went to Epcot almost every day to try out the food booths or go to events. I'm not sure if they will do it again, but the Free Dining offer for that time of year came out in May. We both heavily scrutinize our budget at home so we do like we really like Free Dining because it gets us away from thinking about money.
We stayed at Caribbean Beach Resort. It suited us fine because we really just need a comfortable place to crash. Also, this was or second trip of the year, so the cost of a Deluxe was out of the question. We had a well situated room close to parking and right next to a quiet pool and laundry. We were ill-prepared for how hot it was so I ended up doing a few loads of laundry so we could wear our "coolest" clothing again.
Our two favorite meals this time were Narcoosees an Raglan Road. Boma was a favorite our last trip, but this time we didn't enjoy it as much because of some waitstaff issues; but I would certainly go again. Biergarten is always fun and there is something for everyone to eat. Primetime Cafe was okay too, but nothing spectacular. Kona is also worth a try, I think I ordered poorly, and our sushi appetizer was the pits, but my BF's food was delicious. Also, you must make sure to get a Fast Pass for lunch at Be our Guest. The food really isn't all that great, but you will certainly want to check out the dining rooms.
My biggest piece of advice is to just enjoy yourselves. If you miss something or wake up late, it isn't the end of the world!