i heard that the hollywood hotel is filled with tour groups from the mainland, which could be a nuisance (apologies, mainlanders). cos hollywood hotel is relatively economical in price, ppl are less courteous.
i've stayed many times at the disneyland hotel. everyone in the family (my grandfather, my parents, my daughter) all love it. if possible get a king bedroom, they usually are larger in size & come with a double sofa bed & larger bathrooms. if not, then you can always ask for a travel cot, which comes with pooh bed linens. book the character buffet breakfast of your son knows mickey mouse & the gang. don't bother if he doesn't cos he'll freak out. (most kids who are under 2 who don't know the characters freak out when they see this giant mouse walking around). in the morning, bring your son outside of the restaurant where they serve breakfast (there's a garden & a maze [is that how you spell it? i forgot]) your son is probably too small for the maze but he'll love running around the beautifully kept grassland on the right. then there's the outdoor pool, where they provide life vests for small-big kids. your son will be able to waddle in the water.
i would suggest you try to arrive at the hotel around 10-ish to check in, get your guest ID, book your breakfast (if you're having any) & leave your luggages at the bell desk. usually characters appear at the lobby at arounf 10-11am. then go to the park with the shuttle. play until you watch the parade at 3.30pm (i suggest you go after 17th july, cos they'll start to have a water parade then) then return to the hotel to get your room, freshen up. by then it'll be 5pm. my daughter has dinner at 5.30 & sleeps at 7.30pm. so that's when i order room service, let her watch mickeymouse clubhouse on TV (channel 6, i think). dinner for her in-room, and wind down & bath time for her.
have fun!!