Plucky Survivors See Europe: Where in the World?

When I first sat down to plan my epic road trip, I had a grand vision to do everything – to visit every country and see every sight that Europe had to offer. This is probably going to be a once in a lifetime adventure, so I wanted to do it right!
I immediately ran into the wall of reality, which is constructed out of pesky things like restrictions on visitors’ travel (you can only spend 90 days at a time in the EU during any give 180 period) and money (both the spending of and the receiving of).
So, to keep it under 90 days and not bankrupt myself in the process, hard choices had to be made.
The nature of a road trip means you don’t get to spend enough time in any single location to adequately explore it, but I started my plan by identifying major cities where I wanted to see and do more than an overnight would allow. I wound up with a tiering system, of sorts – places where I wanted to spend three or more days were Tier A (London, Paris, Berlin, Amsterdam, Barcelona, and Lisbon among them); places where I wanted to spend 2-3 days were Tier B (Rome, Vienna, Prague, Munich, Venice, and Porto included); and then everything else, where I could probably get by with just an overnight if it couldn’t work any other way.
Then, to figure out timing, I identified places that had events I wanted to experience, including things like the BST concerts in Hyde Park, the gay pride celebrations in Paris and Barcelona, and World Pride in Amsterdam. This was a long list, and I was unable to figure out how to make most of it work, but I plotted the big ones and designed a rough itinerary with those events as tentpoles.
This necessitated a route that isn’t exactly direct. Would it have made more sense to do something like have Paris, London, and Amsterdam all next to each other? Yes, but that didn’t work on the timing, so I wound up with a crisscrossing journey. In the end, I kind of like it better than if I had done a (relatively) straight line. It forced me into exploring areas that I wouldn’t have seen otherwise.
Then came the really hard part, filling in the gaps between those Tier A and Tier B cities. I tried to stick to a baseline of not wanting to drive more than 250 miles on any single day if I could absolutely avoid it. This would allow me to leave whatever city I was visiting in the morning and make it to wherever I was going by early afternoon, so I had time to actually see the place where I was parking the car for the evening.
That didn’t always work. The itinerary is 72 days long and includes 31 days of driving from Point A to Point B (and a few days of side trips from a location that I’ll be in for more than a couple of days). Of those 31 days of driving, seven are more than 250 miles and a couple are just over 400. The good news is that on most of those days when I am driving longer distances, they are either preceded or followed by days where there is no driving at all.
By the end of it, I developed an itinerary based on the above criteria and I was confident I had it all figured out.
Then came the actual planning part of the process – picking hotels to stay in, sites to see, and things to do. That’s when I realized that that my confidence was misplaced and I was a fool.
Next: Planning and Research and Maps, Oh My!