Thanks for the advice so far everyone! If anyone else has any opinion about the matter, please feel free to comment, since I'm still so undecided about all of this!
Seriously, it goes back and forth every hour. Last night I said to Brandon that going in May was stupid, and he just gave me an "I told you so" kind of look...then today, I thought about it and wanted to go in May again, so I texted him while I was at work and told him and "I don't care what we do, just stop talking about it".
I honestly think at this point, he really doesn't care. 
I'm thinking of actually writing a pros and cons list, so I can have it all out in front of me and make a decision that way. As you can probably tell, I'm the worst decision maker ever! 
Oh yes, one more thing! Remember how I said Brandon has been out of work since September with a foot injury? Well, he's going back to work tomorrow (only half days for a while, but they're giving him terrible hours...7-11 at night) so he had to go to a foot specialist today to get certain shoes and inserts and everything, and the doctor did an xray on him at an angle that none of the other doctors have done in 4 months...turns out he has a broken bone in his foot!
He said the doctor he saw today was really mad that no one saw that in 4 months! It's like 95% healed so he's ok to go back to work now, but still, can you believe that! Just thought I'd update you since I mentioned it a few weeks ago, before our December trip!
If it was my choice, I would go for the one long trip. You can stay at a Deluxe, be there for F & W Festival AND the Christmas decorations (if you go with November instead of September), you'll have more time to save, and Brandon will be more excited to go. You don't want a repeat of 'Boring Brandon," do you?

It sucks that you won't get another use out of your APs, and I know it's hard to think about NOT going again in May, but I think ultimately you will be happier come September or November.
Well, we would only go in November if we did the 2 trips. If we do one, it will be in September so we could use the AP's. They actually expire October 5, so it could be like last year where it was the very end of September into October, but I was going with a whole week in September since it's value season still and the deluxes are $500 cheaper. (Which I think is insane that it changes that much! How do people afford deluxes in peak season!!!

Discounts only get you so far...)
I think one long trip as well, but that's definitely our preferred touring style! And I would love to stay at the Boardwalk resorts. Maybe right at the beginning of Food and Wine? The Tower of Terror 5k sounds fun as well!
I love long trips as well, but at the same time, I love trips to Disney multiple times a year! So it's a tough decision! The only thing I'm really sure of is, I LOVE going in November. It's my favorite time to go. I like May a lot, and I like September, but November is amazing!
Ultimately it's going to be your decision but I know what it feels like to "deal with" a Disney trip being so far off in the distance-and not knowing what to do with yourself until then. That being said, I think you should do one long trip this fall. Might I also suggest trying to rent DVC points to save even more $$.
Pay down/off those credit cards and get another use out of those APs! Both are great financial decisions and I'm sure when you're on your trip this fall you will be happy with your decision.
Now, what you really need advice with is, "What to do to fight the Disney blues". I like to make lists of all of the restaurants that I want to try, all of the new things I want to experience, our must dos, play with dates/resorts/costs. Start a PTR and share memories from your past trips.
Renting DVC points is a good idea, but it's so complicated! If I was going to do that, I'd like to use someone that I know, or that someone I know knows (if that makes sense!)
It seems like one long trip is the sensible decision here, but here's the thing...2 shorter trips costs almost the same as one long trip! And when I looked into renting points, I'm pretty sure 2 shorter trips came out cheaper than one long trip (although I only priced that out for November, not September, which I should do...)
What would be the most sensible option is to do a long trip in September and stay in a moderate. When you compare mods to deluxes, it makes you wonder how anyone can every pay deluxe prices.
I love all of your suggestions to fight the Disney blues!

I can't wait to start a PTR but I can't even think of doing that til I finish my 2 TR's going on now!
I vote for one trip in the fall. I would go in Sept so that the APs get another use. The TOT run sounds fun too.
I think if you make Brandon go back again in May, you'll both be miserable and he'll turn out like John who is still on his 10 year ban of Disney.
If you just do one trip you can stay at a deluxe. I think you should try AKL, it is a great place to spend some time out of the parks.
I wouldn't plan a Nov. trip if you will have to buy tickets again. That would just annoy me, since I just had a perfectly good AP that really went to waste.
Well I knew you would vote for one trip!
I'm not sure how it would go if Brandon went in May. I think he was so annoyed in December because we were just there like, 8 weeks earlier. At least with May it would be like, a 6 month break.
I do want to stay deluxe, but at the same time, they are so expensive compared to the moderates. When you compare values with mods, it's not that much of a difference, but the difference between mods and deluxes is ridiculous! I'd like to look into renting points...and I'd like to stay at AKL sometime, but if we're going during Food and Wine, I'd want to be at an Epcot resort.
Paying for tickets in November is annoying, and that's a big reason I wouldn't want to do the 2 trips. But, I already got a bonus trip in December, and I only bought those AP's because I thought we were going in May, I assumed our only trip this year was going to be May! I had no idea I'd want to go in the Fall again!
totally the sept trip. ill be there sept 20 -30 and i love september and you can get the first unofficial day of food and wine. I think maybe dont do may bc he will totally be burnt out of disney. either just sept or november! plus pay off credit cards and then start saving for your deluxe hotel....Jenn
I like September too, and I'd love to be there for the opening of the Food and Wine festival! We were there last year for the "soft" opening of the F&W fest and it was so nice being there before it officially opened, that's a big reason I picked the last week of September! That and low crowds and value season!

Too bad it's still so hot!
I guess I am in the minority. I think I'd do the two trips. You can enjoy the milder weather in May and most kids are still in school; and in Novmeber you can catch the tale end of F&W as you said and see some of the Christmas decorations.
Personally, it doesn't bother me not staying at a deluxe...I like my moderate and am quite content there. Also, the trip in September is part of the time frame we were there and it just seemed so much more crowded this year...although that could have been we were closer to F&W (which we've still never done) and the fact that it was the 40th anniersary. We are going a little earlier this year (we'll be there September 14-21); if I'm not happy with this time frame, we'll be going back to the Labor Day period whether Mark likes it or not.
***Also, you know that you'll get there in September if you do the one "long" trip and want to take another trip for the Christmas decorations and Brandon may not agree to that.
I'm surprised you're the minority saying take 2 trips, I thought almost everyone would say do 2 trips!

I've only been in May once, but I really liked it, the Flower and Garden festival is a lot of fun! And November is my favorite month to visit!
Haha, I'm not a deluxe snob or anything, I just really like to stay at them if I can! I'm happy at a mod, I'm happy at POP even, I loved it there! But there's just something about the deluxes that makes me really feel like I'm on vacation, away from the real world! I mean, I get that at the values and mods too, but...I just love the deluxes!
I do know that if we go in September, a Christmas trip is NOT an option this year. He'll be back at work, and I'm not using any more of his vacation days for a trip in December, I'd rather save them for next year. Another con against a September trip!
