For those worried about longer splits, they max out the reservation for any room at 30 days.
But you can book a second Lead starting the day the first lead ends.
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I woke up in a panic that my lead didn’t cover the length of the trip and that I would need to book more. Turns out I had already panicked about it before and made two end to end ressies to cover length of stay.
Go Past Me.
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I don’t think that works? Wouldn’t you need to book leading reservations that overlap by 10 days to retain the +10 advantage? 
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That certainly crossed my mind this morning.
I have 5 reservations at 3 resorts (that I’m keeping), but because of the length of stay, I’d end up needing 3 leading reservations if I were to truly cover all my days.
Booked (keeping)
12/07- 12/21
12/21 - 12/23
12/23 - 12/30
12/30 - 01/12
01/12 - 01/26
Leading
11/27 - 12/26
12/26 - 01/25
So maybe I should do
Leading
11/27 - 12/26
12/16 - 01/15(?)
01/05 - 01/26
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What I want to know is: How many of these days are you going to eat at Disney restaurants? Partially because I wonder if you could consolidate your leading reservations so you don’t need one covering literally every day of your trip. And also because holy hannah, that’s a lot of eating out. 
(This from a guy who eats out every day for lunch at at least once on weekends.)
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I want to be you.
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You’re spending 7 weeks straight at WDW?!?
I think my mind just shut down completely… 
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So the answer is all of them.
Probably.
We will probably eat in the rooms breakfast/snacks. Lunch will be quick service or Grubhub/postmates. Dinner will be table service almost every night unless we’re too tired and we call an audible day of-ish.
DH loves a good sit-down. Preferably someplace with good/amazing food and a nice drink. If the food’s just ok, we’d rather just quick service and move on.
We just got back from a 9 week trip 2 months ago. It was amazing, other than my kid didn’t want to leave the room most days in protest of us being away from home and his friends for so long. He tries it again, I’ll leave him home and take @galuchies_463555 instead.
When the pandemic hit we closed down the office and DH not only worked from home but then started a new (and more successful) software company that lets us work from anywhere. He and DS are both the weirdest eaters. And with NV locking down and DS full-time homeschooling, I was going crazy cooking 9 meals a day to keep everyone happy. So I gave up and told them if they didn’t eat what I was cooking, they knew how to Grubhub. And Grubhub they did. Disney isn’t too far removed from that.
This is probably the last time we do a trip this long for a while. I’m working on talking them into Adventures by Disney which is a much shorter 8 day excursion. But then DH can’t work while adventuring, which was the main draw of Disney World. We both could work during the day in the room and roam the parks at night, which was nice because in Vegas the window for enjoyable walking weather is finicky at best.
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I’m in
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So now that we established that I’m basically using WDW as an office, and you wanted to eat out every evening, would you use those three last leading ressie dates and then delete unneeded dining reservations as needed?
The last trip I only had a leading that covered the first 2 weeks and then I was scrambling for same-day anything in January.
(BTW, I’m super uncomfortable sharing all of this. I know it comes off as pompous and I’m just trying to get good reservations to keep DH happy so he wants to keep coming back. I can count on one hand how many times we’ve been on an actual vacation in the last 18 years and we’ve never gone for longer than 2 weeks before this last trip. The pandemic made us shift priorities)
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Oh, this totally makes sense now… 
Hey, everyone here is rooting for you! At least, I am!
For simplicity, I think I’d keep your existing leading reservations and just add an overlapping one.
Maybe @Jeff_AZ can check my napkin here?
Current:
11/27-12/26 (covers 12/7-12/26)
12/26-1/25 (covers 1/5-1/25)
Add:
12/17-1/4 (covers 12/27-1/4)
(Note: 1/26 should already be covered by your actual 1/12-1/26 reservation)
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I couldn’t do 1/5 to 1/26 because the dates aren’t open yet unless I start a reservation in December which goes to your overlapping one. Which I wish I read before I modified it. So now I have a 12/7-12/26 and a 12/16 to 01/15.
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Ok, grabbing a new napkin…
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Which honestly should be good. The end of January wasn’t super hard for most non high demand places unless I was trying the day of.
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Is that first one 11/27-12/26?
If so…
11/27-12/26 (covers 12/7-12/26)
12/16-1/15 (covers 12/26-1/15)
*1/12-1/26 (covers 1/22-1/26)
*actual reservation
So 1/16-1/21 is your only gap, I think? So a 1/6-1/21 reservation should cover that. If you decide you need it. Probably depends where you want those days.
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All I can say is that I really want to do this someday (live at Disney World for a month or two). I might have enough saved up and my kids might be old enough for it to work in like 10 years, or maybe just wait till DD3 is out of the house in ~15.
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Yeah, my DS12s will be gone in 6…
“Sorry…had the empty nester blues…had to do it!”
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I’ve got a 17 high school grad and a 14 year old freshman. I’m so close I can smell it. I’d be down for a month at Disney anytime. I’ll just leave the college one in charge of the high school one…I mean what could go wrong!!! 
(I am just kidding but three more years and two more months!)
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I would do three overlapping reservations just to make sure. It was nice to casually make reservations at 60+10 sometime during the day, every day rather than waking up a oh-dark-thirty.
Although, you have another thing that will make it easier for you, flexibility from the long stay.
I personally think that rather than reserve the cheapest, I reserved the most availability. I don’t give a hoot about Disney since they created this mess. But, I don’t want to stop someone from getting a hotel reservation that they wanted.
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He is a good choice but there may be others who want to be included too 
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