BTW, I can't believe that you made 44 trips in 33 years! Wow! You are a veteran. If it's ok with you, when more questions pop up, I'm going to pick your brain! Again, thanks everyone for the very useful tips and please keep them coming!
Feel free to do so, Lap!

Most of those trips came when I was a kid, back when there were only 4 hotels, the villas, and 1 park!

can you imagine? LOL But i have been to WDW four times in the past five years, with another coming up soon!
Okay; here's a couple things to consider about UPH's/length of stay. As the others have said, you need to think about the features that are bundled in with them: what are the ages of your kids? Will you really be planning time to go to the waterparks and DisneyQuest? If not, these are options that it may not be worth paying for. Also, if you do not plan a repeat trip to WDW within 11 months, I would suggest foregoing the Annual Passes. Unless REALLY great room rates pop up (and you never know in advance, and i think it's a lot less likely during the busy season over the summer) they will cost you more than you will get out of them.
It is VERY hot in June, also you need to find out about possible senior nights at the MK (when local high school graduates take over, basically) that may occur during your stay, and plan around it.
Breaks during the day are a must, for mom and dad not just the kids, hauling strollers/diaper bags etc is taxing and above all, you have to be sure you all keep hydrated! It's easy to lose track of time and not realise someone is getting dehydrated until they're already feeling sick.
Once you have your dates, read up a little in the book, let us know what questions you have and I and others too will be happy to give you input!
sorry to jump around too, my MS brain does that a lot LOL.
If you have small children and really want to get the most out of your trip (and you said you don't know when you'll get to WDW again) you may want to consider really splurging on a Monorail (deluxe) hotel if you can afford it. Especially when its really hot, being able to get back to the hotels quickly is a huge advantage, and also they have nicer amenities and rooms. But it's the convenience of travel that really sells my family on the monorail hotels.
If you tell the approx ages of your kids and how many kids you have, that will help us give suggestions that will be more helpful.
Most of all..enjoy every step of the planning! Your trip will be magical when all is said and done
geek