What a wonderful trip report! Thank you so much for taking the time to write it ~ sounds like you had a great trip and took a few negatives in stride
We were down for Dapper Days a few weeks ago and dealt with very similar crowds and heat ~ it certainly changed the way we normally toured but we still had a great time.
I learned 2 things about the monorail that weekend that I'm sure most DL regulars know already but were new to me. I have posted about these but will include here, also:
1. The monorail doesn't run if the temps are over 95 or the heat index is over 97 ~ so walking back to the monorail station in hopes of taking it back to DTD and enjoying a short walk to your hotel in the heat of the day is not an option and only adds to your walking. I was told by a CM that it is due to the monorail not having a/c like those in Florida do and it can become dangerously hot on the monorail, especially if it gets stopped for any length of time with guests on it. Note: the CMs at the TL station telling you it is closed will helpfully suggest you head over to the train station and ride it back to the front of the park ~ a great idea, unless they have told 500+ guests before you the same thing and you have to wait for quite a few trains to actually be able to board one. Better to suck it up and push through the heat.
2. The monorail doesn't run prior to and during the fireworks so walking back to the monorail station in hopes of taking it back to DTD and having a short walk back to your hotel and avoiding the crush of humanity filling Main Street for the fireworks is not an option and only adds to your walk. Once I stopped and thought about this it was obvious as the monorail travels through the fireworks fall out zone but I had never really thought about it before.