Well, I just realized that you're the same person with the stroller questions. You've got to put your hotel in your ticker! It helps us answer you.
I don't know who's giving you advice about DLR, but you should shush them in the future. We live in WA, so definitely not local, and we go on vacation there! There are Australians, New Zealanders, Europeans...people from all over the country who visit. It's NOT just locals. And FYI, my cousins are locals to WDW and go to WDW often! My one cousin and her now-husband courted for a year with WDW trips.

Locals are everywhere at every park.
People do pin trading all the time. Hubby enjoys it, and tends to gravitate towards the CMs working in stores. Ask if they have a trading lanyard; not all of them do, but many that do keep them behind the counter instead of around their necks. I don't go near the people standing or sitting at tables with big pin trading books, because they seem to have profit-reasons for trading...they also glare at you if you look at their books but aren't wearing a lanyard (because it got too heavy with the camera around your neck and you put the lanyard in your purse). the ones I've encountered at least.
Stop at City Hall to deal with the GAC.
People are people...some are going to look extra at someone who looks or acts in a way that they didn't expect... I don't think that DLR visitors will give extra-rude looks than WDW visitors.
You'll get Magic Morning each morning it's offered during your stay. It's generally offered on the T and S days, so Sat Sun Tues and Thurs. If you're getting into town very very early on a MM day, you can check in and take advantage of the MM...again, you'd have to be there very early. If your day of check out is an MM day, you get to take advantage of it. MM gets you into DL one hour early on those days, and Fantasyland is open, along with parts of Tomorrowland (Nemo, mainly, and Buzz I believe). The other lands are not open for it.
If you want to start each morning in Tomorrowland, you can take the monorail in. Though on MM days that might not be the most helpful, as the monorail sometimes doesn't leave until opening time, which gets you in after the walkers. If you are ending the days in Tomorrowland, it's simple to get the monorail back. But if you aren't going to be in Tomorrowland each time, you'll have to figure out if walking there to get the monorail makes more sense than just walking out and through DTD to get to the hotel.
Check out the Disneyland section of the info-dis (wdwinfo.com) as well as allears.net...in my opinion allears is better than the dis for menus (wdwinfo is missing many items and menus). That will show you the various restaurants around DLH. If you guys swim, DLH has a pirate-themed pool. We cannot wait to try that out.