Quick question for the "on your own" night in Hollywood (day 2). Is a 6:30 PM dinner reservation late enough to be done the afternoon activity? There's a restaurant about a 15 minute walk from the hotel that I was able to get a table at and I wanted to be sure the timing was good.
In my experience, it is difficult to schedule any dining reservations (inside or outside the DLR) during the tour, because the schedule, although planned, is not guaranteed to run exactly as planned. For example, if a part of the backstage tour cannot operate at the planned time (for various reasons), they may move it to a different time, or replace it with something else.
However, if you DO schedule something, just let your tour guides know (preferably the night before, or that morning), and they will do their BEST to accommodate your dining reservation. You may miss something, you may not.
The only time I distinctly remember having a large chunk of time on our own was when we visited Star Wars Galaxy's Edge (it had just opened a couple weeks earlier), and they gave us a long time on our own there.
Also, so you know, even though they call it "on your own" time, most of the time they still schedule something fun that you can do with them (optionally). For example, in hollywood, they told us we can meet them in Ghiradelli's for ice cream. On another tour (I've been on the tour twice), they instead invited us to go with them to the Wax Museum, which was optional.