I love answering these types of posts. I was you 3 years ago. 7 trips and ove 50 park days to WDW - I like to think of myself as a veteran. Except I left right before FP+ started. Yuck. Just the thought of all the extra planning ruins the magic for me. Anyway.....
DL is waaaayyyy different than WDW. First, no FP+, so no planning for rides each day. You just come in and play it by ear. It's soooo nice this way. You have freedom to go wherever you want, whenever you want.
Second, as a WDW vet, I HAD to stay onsite for our first trip. To do anything else just didn't click in my mind. So we stayed at Paradise Pier. And while it was a nice hotel, it really never had that Disney feeling you get at a Moderate in Orlando. No escape feeling. And then you have to walk across a city street to get to the parks...certainly no bubble there. We've even stayed at the DL Hotel....still couldn't get that "magic bubble" feeling you get at a WDW resort hotel. I've heard that the Grand Cali gives you that bubble feeling because of it's Disney World-esque feeling and proximity to the parks. But for the price, we've never tried it and probably never will. It's just too much money.
We've stayed in a few "off-site" hotels on Harbor Blvd. Some were OK and one was great. And that ONE is the HoJo Anaheim. First, we love getting the superior rooms because you get a view of the parks. You can see right into Tomorrowland, have a view of the Matterhorn, and watch the monorail go by all day. And I've never seen this room for over $200 night. Plus it's about the same distance to the parks as the Paradise Pier and some of the rooms at DL Hotel. So the walk isn't bad at all. Plus it has indoor hallways in the tower rooms. On top of all that, it even has a mini-water park that's great for kids 10 and under.
As for dining, this is another big difference. I actually miss the
DDP at WDW, where I'd eat at a TS everyday at awesome places like Tony's, Tusker House, Crystal Palace, Le Cellier, Prime Time 50s, Chef Mickey's, and my personal favorite Liberty Tree Tavern.
Disneyland just doesn't seem to have places like these. My favorite TS places at DL are Rainforest Cafe and Ralf Brennen's Jazz Kitchen, if that gives you an idea of what Disney itself actually offers. The one TS place you have to try if you're doing DL only once is the Blue Bayou. Think San Angel Inn, only inside the Pirates of the Caribbean ride, and it actually has good food. It's pricey, but it's worth the experience.
As for counter service, this is about all we do when we're there. There's a pretty good variety of food. Definitely try Flo's V-8 (50s style restaurant) and Pacific Wharf Cafe (clam chowder bread bowls) at DCA. At DL, Plaza Inn has some great fried chicken and Village Haus has a good pastrami burger and kraut dog.
My best advice to all WDW vets, I know you won't be able to take....because I couldn't take it until maybe my third trip. Relax. It's a different pace at DL.