Wow, this sounds wonderful!! I'd love to hear more about this. How is your DH able to get that much time off in one calendar year? Do you rent a home down there or do you stay in a hotel? Do you fly down and rent a car for the month, or do you drive down?
You had lots of good practical suggestions in your post. Thanks for taking the time to share them with us!
Well, we homeschool so we simply take school with us. My DH doesn't love Disney as much as the girls and I, so he came for 10 days on our last trip and actually doesn't want to come for our Nov/Dec trip....he's going to take Thanksgiving week off of work and remodel the girls' bedroom as a surprise for them instead....in full princess style. That's HIS idea of fun, lol.
He travels a lot for work, and we often accompany him, so combine that with a like not love of Disney, and he's happier at home. Sounds cruel to some of our friends for the girls and I to go for a month without him, and especially over a holiday, but well, he's ok with it (and was the one that suggested the dates because it gave him more time to remodel) so we're ok too.
We live on the west coast so yes we fly. I wouldn't mind the drive, because there are a lot of things we'd love to see between here and there, but it would take wayyyy to long with all the stops we'd want to do, we could probably take a month just to get there. And of course, even last year when gas was a little lower, between gas and hotels it's still cheaper to fly.
DH travels a lot and earns free airplane tickets, so we're using one of those in November. The girls and I won a free trip for 2 to a dinner theatre in Ft Myers, so we're using those to pay for the other two airplane tickets, and we'll spend the Fri/Sat after Thanksgiving in Ft Myers on them and going to dinner theatre Saturday night. We'll be at Grandma's north of Tampa for Thanksgiving. The prize was actually good at 3 different locations around the USA, but of course, we chose the one closest to WDW.
In January/February we stayed in a 4 bedroom house offsite, with a private pool, kitchen, and lots of space to spread out.....all for about what it would have cost us for two weeks at a moderate. The 4 bedroom was too big for us really, so this next time we're staying in a 2 bedroom....still more space than a hotel room, and just as cheap as a value for half the time.
We also rented a van, as obviously we'd need to get to the park each day. We have APs so no parking fees. We got a smokin' deal on a van, it was only a few dollars more than a standard, and since I have a van at home, I went for it. This time around I haven't found a cheap van, but I found a standard for about half the cost of last time, plus we have a free upgrade (though I haven't decided if I want it, we'll see what they have available when we check in).
Even when you add in the rental car to the house cost offsite, it was cheaper than staying at a moderate. And square footage wise we literally had about 8 times as much space (value is 260sf, mod 340sf and the house was over 2500sf) The space was most important to me, but the private pool was wonderful, and the kitchen was really nice too. A month of restaurants only sounds fun....in reality you start wishing for some comfort food from home really quick. We still ate way too many meals at WDW because we wanted to try them, but we also enjoyed a few homecooked meals, and even a couple of "in town" meals. Of course that's a cost savings too if you aren't eating WDW's inflated cost meals.
A lot of people can't imagine staying off site....their opinion is that they will lose some of the magic having to leave Disney property. We didn't find that at all.....we brought some favorite Disney things to decorate the house (it had a few but we wanted OUR stuff to make it a home for a month), and it really felt Disney to us. I've seen pictures of the deluxe rooms and they don't seem to have as many hidden mickeys and Disney touches as our house did! The values definitely do, but we got to stay for a month....so I respectfully ask Who had more magic???
Disney is expensive no matter how you do it.....but it can be relatively affordable IF you are willing to work to make it so. Most people don't believe me when I tell them that our month at Disney, including airfare (which we did have to pay for that trip, we get free next trip), rental van, house, gas, food at Disney and off property, souveniors, P&PP, was under $6,000. That's still a lot of money but for a Disney vacation for that long it's really a bargain. That price doesn't include our APs, but we paid for those the summer before we went and bought them before the price went up. We'll be using those for another month long trip too, so I guess you could add in 1/2 the cost for the Jan/Feb trip, so that'd put it just over $6,000. Our budget for Nov/Dec is only $4,000.
We've been very lucky to get to travel with my DH with his company picking up the tab for hotels, almost always your highest expense.....he usually flies and rents a car (company pays), we drive so we have our van to use to explore while he works. He really hates living in hotels so he feels that having us there when he gets home from work is great! And we do stuff together evenings and weekends so he gets some fun. He gets a per diem food allowance, but we always get a kitchenette room and I cook, so his allowance often pays for most of the food for all 4 of us. We usually have one or two meals out to sample the local cuisine, but never chain restaurants. Gas prices are making this more expensive, but it's still a bargain way to travel!
I never use credit cards. If I don't have the cash we don't do it.
It's more important to me right now to make memories with my only child and husband (who is older than me) while we are all healthy and able to travel. 
What I'm trying to say is, don't make yourself crazy or feel guilty if you don't get back to WDW until your son is older. Getting out of debt and getting on secure financial ground is the best gift you can give him! Best wishes to you both! 
