Well, we just got back from doing both - first timers with kids 4 and 7.
We stayed 5 nights at Tropical Palms in Kisimmme and 2 nights at PO-Riverside.
We enjoyed our offsite accoms alot because we had a cabin with 2 bedrooms and full kitchen. The atmosphere was very calm and relaxing. The total time to the MK parking lot was 15 minutes, and we never encountered any traffic. The trams/monorail added another 15-20 minutes to the actual time to MK gates and we thought might be a hassle worth avoiding.
We really liked PO-RS and found the atmosphere really really nice. I've never seen a hotel done up like that one was - the grounds I mean. We tried the buses, and they were ok . Took about half an hour to get to the bus, wait for one, then get to the MK gates (actual drive time was 17 mins). It was nice to avoid the trams and monorail. It wasn't nice waiting for the bus, or standing, or sitting with our kids on our laps on a crowded bus. Also not nice carrying them back to the hotel room from the bus stop when they fell asleep on the bus after the fireworks.
Transportation wise - six of one, half dozen of the other. If you stay somewhere reasonably close, I can't imagine you are going to feel that driving in is more hassle than bussing it from Disney (to MK that is). I really can' t imagine it matters at all somewhere like AK, where you just park and walk to the gates. Disney itself is so big, it seems to take as long to drive between resorts and parks as it does from offsite.
We don't consider Early Entry a vacation option (thats our regular life) so we didn't miss it. E nights are something we would probably use if the option was available.
Atmosphere wise - we found returing to some privacy and comfortable space at the end of the day nicer than going back to the hustle and bustle of a Disney Resort. The parks were enough of that. The imagination at the DR was something to see - the first couple hours. After that, it wore off.
Overall - we stayed the 2 days at PO to see what it was all about. It really is something the way Disney does those hotels. I can sure see how people who've never stayded offsite, or only stayed offsite in other (cheaper) hotel rooms would think staying at Disney make a great difference. But our final opinion - having tried the offsite option with the suite comfort factor - a Disney Hotel Room is a nice place to visit, wouldn't want to spend a week there.
After a DR, I would be disappointed with some regular old hotel room in a regular old hotel, I'm sure. So pick yourself a nice suite location close to the parks, and see what a Disney moderate doesn't give you. I'd recommend checking
www.hotelkingdom.com for places such as Vistana Resorts, Vistana Villages, Caribe Royal, Holiday Inn Family Suites (if you have young kids). These places typically get good reviews on this board, and using hotelkingdom will get you into them for definitely less than the rack rate at a Disney Moderate. If you are at all the outdoorsy type - also check out our pick (after considering all of those others) - Tropical Palms (
www.tropicalpalms.com). Nice comfortable clean cabins. LOTS of space compared to a hotel room. Kids liked the cabins more than PO. I thought they'd be sold on PO's pools, but apparently a sleeping loft and lizzards to chase are more attractive.