OK, I am an accountant so I naturally can come up with wonderful spreadsheets so that I can compare things. If you remember, I asked for feedback about including items to do a cost comparison between onsite at CSR and WL and a condo at Windsor Hills. Forgive me if it is long. This is for two adults and two Disney kids
On Site assumptions - park tickets and tax (no parkhopping), regular dining plan, $300 for tax & tips on meals, $50 for groceries, seven nights lodging and tax
Value Season
CSR at 30% off (common PIN discount) - $2,900.80
WL at 40% off (again, common PIN discount) - $3,171.32
CSR with free dining - $2,517.30 (room at rack rate)
WL with free dining - $3,174.96
Regular Season II
CSR at 30% off - $3,017.08
WL at 40% off - $3,456.08
CSR with free dining - $2,683.41
WL with free dining - $3,649.56
Windsor Hills assumptions: park tickets and tax (no parkhopping), seven nights lodging and tax, pool heat (which may not be needed), Dining at Disney which includes dinner at Crystal Palace and breakfast at Akershus and 3 CS at $50/day (these totaled $435 + $150 tax/tip), parking, out of park dining at $40/day, $100 for groceries - this is how I imagine my family would dine
WH total - $2,998.56
So, staying at WH is not cheaper all the time when comparing with a moderate but is cheaper than a deluxe every time.
I did learn that the dining plan would work great for my family because I looked at where we would like to dine with the dining plan and the total cost was about $872 and that did not include any desserts and only one drink for the whole party whereas the dining plan is $756. My food when staying at Windsor Hills would total $765.
Thanks for letting me amuse you. Now the question is, will I stay on site or off and that is yet to be determined.
On Site assumptions - park tickets and tax (no parkhopping), regular dining plan, $300 for tax & tips on meals, $50 for groceries, seven nights lodging and tax
Value Season
CSR at 30% off (common PIN discount) - $2,900.80
WL at 40% off (again, common PIN discount) - $3,171.32
CSR with free dining - $2,517.30 (room at rack rate)
WL with free dining - $3,174.96
Regular Season II
CSR at 30% off - $3,017.08
WL at 40% off - $3,456.08
CSR with free dining - $2,683.41
WL with free dining - $3,649.56
Windsor Hills assumptions: park tickets and tax (no parkhopping), seven nights lodging and tax, pool heat (which may not be needed), Dining at Disney which includes dinner at Crystal Palace and breakfast at Akershus and 3 CS at $50/day (these totaled $435 + $150 tax/tip), parking, out of park dining at $40/day, $100 for groceries - this is how I imagine my family would dine
WH total - $2,998.56
So, staying at WH is not cheaper all the time when comparing with a moderate but is cheaper than a deluxe every time.
I did learn that the dining plan would work great for my family because I looked at where we would like to dine with the dining plan and the total cost was about $872 and that did not include any desserts and only one drink for the whole party whereas the dining plan is $756. My food when staying at Windsor Hills would total $765.
Thanks for letting me amuse you. Now the question is, will I stay on site or off and that is yet to be determined.
We've considered staying at Windsor Hills and still might do so some day. Personally I like the free dining because I don't have to cook and my husband doesn't have to drive around finding an off property restaurant we can get into without a 45 min. wait. The condo idea is really great in terms of the extra privacy which is worth a lot to us. The extra magic hours? Love 'em but usually the kids are too pooped for us to take advantage of them. Your cost comparison was really interesting to read - off property vs. on property. I might try doing the same research for my own family to see how we would fair either way. The biggest saving for us would be eating at home more - but that means more work for Mom and less vacation... 
