The Mrs and I have done Disney on every budget (ranging from collage budget staying at the Red Roof Inn and sharing meals at the park to staying at the GF and every one in between) and we used to have the same debate. Now it comes down to, how much is that time it takes getting in and out of the park worth to you. Are the savings worth getting up earlier, driving to the ticket center (paying for parking) getting on the tram, then getting on the monorail, then getting in the park. Or just hoping on the monorail or bus and being there in a few minutes. To us, especially with a little one, it was a no brainer. I would rather spend the $$$ and save the time. especially at the end of the day with a sleeping child in the stroller. Not having to wake him up, and just sliding him into bed is worth the extra $$$$.
This is my exact reason too, some of you may know my dad has a 3 bed apt at Bahama Bay in Davenport. We all go to Florida but stay at OKW. He gets kind of miffed that he can't stay at his own place but I've said to him that you can't put a price on convenience. He's going there on his own this Saturday just to stay at it. I've said to him if he sets foot on WDW property while there he should remember who will choose his nursing home lol.
And with regard to price, for us it is actually more expensive to stay offsite, even when we stay Deluxe at WDW. I have spreadsheets detailing every penny and cent that would be spent. We love character meals, and with the free dining plan we can do them nearly everyday. We couldn't afford to do it if we had to "pay" for food. Although breakfast isn't included in the package, a $200 gift card is, so we use that to stock our kitchen with breakfast items etc. We got the 35% discount too.
Then there's the cost before you get on the plane. The fuel to the airport, the cost of parking, the inconvenience of driving home after a 9 hour night flight. If you spend over 5k my travel agent takes clients to the airport in a minibus.
And then there's the little things like EMH, having merchandise sent back to the hotel and concierge can give you immediate answers regarding the parks.
But that's not to say it won't change when the kids get a lot older and they meet the height requirements for Uni. We love Disney, but I can't say I'm not excited about going to Uni again. We didn't do it last time as only had 10 days, this time we have 18, and because we only have 14 day Disney tix, we will for the first time ever, do Uni as our first park. I feel like I'm cheating on Walt doing this but I'd rather have MK as the last park we visit.