Thanks for the feedback everyone! I guess the biggest question I have for now, other than how many days, is, is it worth it to stay at the DL hotels or is it fine staying across the street? If we do three days I can about guarantee we won't bother with the early morning extra hour, so thats not a big deal. I like being able to send purchases back to the room, but I don't know that for $150 a night I wouldn't just wait and make purchases on our way back to the hotel. But are there really any other benefits to staying on site? I can swing the extra cost, but at almost $500 difference for the duration, is anything really gained?
Also, if I were to decided to stay on site, when would hotel discounts likely go on sale for then if they are going to do any? Seems like they are just doing end of Summer sales right now.
I haven't even thought about dining yet. We usually don't bother booking dining in advance because we never know what mood we will be in. How bad are they for taking walk ups?
No. Never have been to Cali at all. We did 5 days at WDW a few years back. The daughter doesn't really remember much of anything, so it will pretty much be all new even with close rides.
I didn't event realize you had a DL book. I'll have to order one. But do I get the 2016 book or the 2017 book? lol
Let's take your questions in order of asking
First of all, hotels: I really like the Disneyland Hotel as it is within 10 minute walking distance of the park. The other advantages are the pools, being able to drink at Trader Sam's (which is a great place to grab a drink and small plates meal) without having to go anywhere, and the one hour early entry every day of your visit. This early entry time can be key for getting through the Fantasyland rides and getting your whole family together or Radiator Springs Racers without a ridiculously long wait. Granted, if you get a 3 day pass you automatically get one day early entry so mileage will vary on that benefit.
As far as early entry goes, I recommend you do early entry at least one day (whether you stay on site or just use the ticket option) as it will allow you to get through the very popular/low capacity Fantasyland rides before the regular guests get into the park. These rides DO NOT have any Fastpass so hitting them during early entry is rather ideal.
As far as hotel discounts, given that it is the holiday season I would be surprised if you found any, but I they do occasionally pop up (read as, no guarantees of anything).
For meals, the only two restaurants you would NEED a reservation at are Blue Bayou and Carthay Circle Theater (assuming you want to eat at them) as those two book up early; the rest are easy enough to do walk up eating. Of the two, I would recommend Blue Bayou for ambiance (it is located INSIDE the Pirates of the Caribbean ride) and Carthay Circle for food (duck wings for the win!). Given your daughter's age and that it is your first visit, I would highly recommend Blue Bayou as it is always cool watching the boats float by.
One more thing to point out is that Disneyland has single rider lines on Splash Mountain, Indiana Jones Adventure, and The Matterhorn Bobsleds while California Adventure has single rider lines on Radiator Springs Racers, California Screaming, Goofy's Sky School, Grizzly River Run, and Soarin' Around the World so try to use those to your advantage, if possible. Utilizing single rider lines, Fastpass, and early entry my wife and I were able to see 2 parades, see the fireworks, see Fantasmic, see Mickey and the Magical Map, see the Royal Theatre Presents: Frozen, have a nice sit down meal at Blue Bayou, and still get on 21 rides during a level 9 busy day (according to Touringplan's attendance numbers).