Just to summarize Adam's walk and talk from earlier today and what to expect for the rest of the year:
Expect more Woopeats (Disney & baseball) for the rest of August.
Fly to Atlanta late August for Dragon Con, spend 5 days there.
Fly to SoCal to go check out the various haunts there, and attend D23. Will be there about 2 weeks.
Mini roadtrip for latter half of September, to at least Salt Lake City and possibly more Rays' away basebal games.
DVC hotel stays and reviews in October.
More Woopeats again in November and possibly another mini roadtrip.
Break from the channel in December to spend time with family.
Based on the Rays September road schedule, I don't think he actually looked at where they're playing, and was just spitballing, because the timing is going to be hard, unless he 'cheats' on the 'road trip' and flies to one of the cities.
Rays September/October road schedule:
9th-11th in New York. Imagine a cringy ATW honors 9-11 at Yankees stadium. But if he's going to D23, which starts on the 9th, this is unlikely
12th-15th in Toronto. That's a long-ass drive from CA or Florida, if he leaves immediately from D23. He could always fly direct, like with Seattle, but is that really a 'road trip' then?
27th - 29th in Cleveland. Depending which route he takes, he could detour to Pigeon Forge again on the way, and it would be close-ish to his sister in Indiana if he wanted to go there on the way back.
30th - October 2nd in Houston. The only place that logically makes sense on a route to/from Salt Lake from Florida, even though it isn't on the direct route.
October 3rd-5th. End the season in Boston. He already did Boston so this seems unlikely unless the Rays are eliminated from playoff contention and he needs one last 'fix' before becoming a Braves fan again for the PostSeason.