Cheapest way to do Disney?

[KalamityJane]

We are getting APs at the end of Nov 2014, and have a 2.5 week trip planned then.

DH gets 3 weeks of vacation each year ( 3 weeks from 2014, of which he will have 1 week left after the vacation above) and then another 3 weeks in 2015.

The youngest will be 3 just after our APs expire, so we count as a family of 4 +1 for Disney's resort accounting.

We live in the PNW, but my family is in Orlando, so I'm killing 2 birds with 1 stone by trying to make it down there and get the most out of the APs as possible, however the plane tickets are $$.


Timing
Should we do -
Option A:
Nov/Dec 2014 - 2.5 weeks
April or May - 1 week
September (this will likely be just the kids and I, DH will use his week to go hunting, so I could conceivably stay longer)
Nov 2015 (thinking mid Nov) - 2 weeks

Option B:
Nov/Dec 2014 - 2.5 weeks
September (DH with us for 1 week, the kids and I stay longer)
Nov 2015 - 2 weeks

If we go in September, I'm probably going to do at least part stay at Wyndham Bonnet Creek. I can totally get one of my younger siblings to help at Disney if DH is not there, they would be thrilled to go and can get the FL resident price for tickets.


Plane Tickets

Plane tickets in both April and September should be ~280-300 each person. I'm thinking the best way to get tickets would be to sign up for the Southwest credit cards, and then use the points and companion pass to book tickets, that should help costwise, plus we have an Alaska Air credit card and since we moved, Alaska doesn't have convenient flights to our new town, plus it's the only airport within 6 hours. Southwest, however, does have very convenient flights to MCO, so I know we would get our money's worth out of points earned on it. I will be using our Alaska miles to book half of our tickets for Nov/Dec 2014, so we only will be paying for the tickets out there for the 5 of us.

Resorts
We are staying DVC and FW on the first trip, so that is set, however, if we go in April/May, that would not be a good time to go DVC. Should I look into booking a bounceback offer in Nov/Dec 2014? We would like free dining, but I honestly don't think that it would be the most cost effective as we like to stay deluxe. Also, my kids eat like birds. The kids would be almost 7, 4 and 2 in April 2015.

We will be renting a car more than likely on subsequent trips, but not in Nov/Dec 2014.

Any awesome tips on cost effective summerish stays? I'm trying to keep them as low $$ as possible while still providing a quality vacation.

 

[Marionnette]

We are getting APs at the end of Nov 2014, and have a 2.5 week trip planned then.

DH gets 3 weeks of vacation each year ( 3 weeks from 2014, of which he will have 1 week left after the vacation above) and then another 3 weeks in 2015.

The youngest will be 3 just after our APs expire, so we count as a family of 4 +1 for Disney's resort accounting.

We live in the PNW, but my family is in Orlando, so I'm killing 2 birds with 1 stone by trying to make it down there and get the most out of the APs as possible, however the plane tickets are $$.


Timing
Should we do -
Option A:
Nov/Dec 2014 - 2.5 weeks
April or May - 1 week
September (this will likely be just the kids and I, DH will use his week to go hunting, so I could conceivably stay longer)
Nov 2015 (thinking mid Nov) - 2 weeks

Option B:
Nov/Dec 2014 - 2.5 weeks
September (DH with us for 1 week, the kids and I stay longer)
Nov 2015 - 2 weeks

If we go in September, I'm probably going to do at least part stay at Wyndham Bonnet Creek. I can totally get one of my younger siblings to help at Disney if DH is not there, they would be thrilled to go and can get the FL resident price for tickets.


Plane Tickets

Plane tickets in both April and September should be ~280-300 each person. I'm thinking the best way to get tickets would be to sign up for the Southwest credit cards, and then use the points and companion pass to book tickets, that should help costwise, plus we have an Alaska Air credit card and since we moved, Alaska doesn't have convenient flights to our new town, plus it's the only airport within 6 hours. Southwest, however, does have very convenient flights to MCO, so I know we would get our money's worth out of points earned on it. I will be using our Alaska miles to book half of our tickets for Nov/Dec 2014, so we only will be paying for the tickets out there for the 5 of us.

Resorts
We are staying DVC and FW on the first trip, so that is set, however, if we go in April/May, that would not be a good time to go DVC. Should I look into booking a bounceback offer in Nov/Dec 2014? We would like free dining, but I honestly don't think that it would be the most cost effective as we like to stay deluxe. Also, my kids eat like birds. The kids would be almost 7, 4 and 2 in April 2015.

We will be renting a car more than likely on subsequent trips, but not in Nov/Dec 2014.

Any awesome tips on cost effective summerish stays? I'm trying to keep them as low $$ as possible while still providing a quality vacation.

Do you want the cheapest way to do Disney or are you looking for the cheapest way to accomplish 4 cross-country trips with deluxe resorts stays? I'll be frank and say that "cheap" doesn't belong in the same discussion with the number of trips combined with the type of resort you prefer.

If you want to get the most for your money, make fewer trips and stay longer. Instead of 4 trips where you stay 2 weeks, 1 week, 1 week and then another 2 weeks, why not go twice and stay 3 weeks each time? You'll save a ton on money on airfare for 5 people!

Instead of staying in a small onsite DVC unit for the 2nd trip, rent an entire vacation home with its own private pool and game room and invite your family to spend time with you there. VRBO and HomeAway have some awesome vacation rentals in the Disney area.