Reading this thread just makes me wish we could go back to DLR. I'm in knots over our upcoming first trip to WDW, because it's so much more stress and planning to the minute--and we're staying 10 days and still can't see everything because everything is so far apart and we'll lose so much time traveling from place to place.
Please believe the DLR forum sticky threads (and the PPs here) about the differences between DLR and WDW. You absolutely want Park Hoppers. The parks are not separated at all, nothing like WDW. We bounced back and forth multiple times a day for different entertainment and popping into favorite rides. And you can get any ADR you want. Also remember that it has more rides than WDW (or did in 2013).
We went in Oct-Nov 2012 and Aug 2013. I highly prefer fall and Halloween, but was pleasantly surprised at how nice August was. I hate summer, hate heat, am disappointed to see that we'll need shorts in Dec in Florida. August in SoCal was fine. The humidity makes a huge difference. And of course, it never rained! Both trips were long stays, split up with side trips elsewhere, Carlsbad and Legoland for one trip, NoCal Bay Area for the other. If we went now that WWoHP is open, we'd be going to Universal for sure.
Tropicana, family suite: It was fine. It is totally motel, both in feel and in technical definition. But we upgraded to the nice suite with a fireworks view (so up in the very front), and the jets in the tub worked. Everything it lacked in finer appointments or breakfast offerings was made up for in only being a five-minute walk to the security check point. Walk out the door and cross the street, you're there.
Residence Inn Maingate: Love this place, disappointed to see the steep price climb here (and everywhere else in the DLR area, it seems like) but still would use again. We stayed in a one bedroom, and ate at the hot breakfast buffet every morning. Nice beds, nice sheets, quiet, close enough (15-20 minute walk while pushing a double stroller) for easy afternoon breaks.
We ended both stays with short stints in DLR hotels, which are not any closer or more convenient. The special entrance at GCH is understaffed for the huge demand in the morning, so we got in faster by going to the regular entrance. (It's totally fine at any other time of day.)
Paradise Pier: We had a great time there staying concierge level with a park-view room. But the club is small and always packed when the food is out. We did our character breakfasts the mornings we were there since we had lost the lovely Residence Inn buffet. The park view is amazing, day and night. I might be a bit spoiled, though, because we had a minor room problem that got us upgraded from a regular park-view room to a family suite. ;-)
Disneyland Hotel: It was definitely fancier and grander than PPH, and of course we loved the magical headboards. We had a partial view of the fireworks that underwhelmed. We only took the monorail into the park once because it really was not quicker, just a bit of fun. I preferred PPH for its more laidback feel, but I'm pretty sure I'm in the minority.
Oh, except for the POOL. We did a half-day at the pool with a cabana, and it was glorious!