We've been to WDW over a dozen times and have stayed onsite only once, so I'm probably not your most unbiased advisor, but...we didn't love being onsite (don't flame me!). We stayed at POFQ and while the mattresses and sheets were superior, it was, after all, a hotel room with 2 double beds and a teeny tiny bathroom, one TV, external corridors, and a small round table with 2 chairs. The busses were a nightmare in late June...took 1.5 hours to catch a bus to Magic Kingdom and then the monorail to the Polynesian...a 20 minute drive from most off-site hotels, maximum. Then, there was the wait for the bus BACK to the resort at park closing...1 hour for bus after Fantasmic, and it was packed to the gills with hot, tired, cranky people. I LONGED for my own car to whisk me back to my hotel where I could be cool and comfortable. Regarding the food court at POFQ, I was amazed by all the variety available; definitely not just burgers, fries and nuggets, but the prices! You pay for convenience and theming, but you really pay for the Disney name. Regarding Disney transport, to be fair I'm never happy with hotel shuttles, either. They are never there when you need them, and often take a circuitous route...although as long as I have a seat, this is OK. Travelling with a 4yo and a 72 yo (I've done both), I'd find a great rate on a hotel or suite (check hotelkingdom.com, skyauction.com, discounthotels.cc) and then get a rental car; mousesavers.com has great codes and tips for keeping the cost low- check transportation and budget boards for tips too.
When will you be in WDW? We are goind Dec. 8-15, and my mother-in-law (no, this is a good thing!) from Cleveland is considering coming also! Maybe we'll see you!