Awesome post!
Strange, I've had no problems yet at a handful of airports (neither free wifi ones nor Boingo hotspot ones) and I'm at a Hilton property now that requires you to hit a particular website first then click OK, and that's fine too. Mind you, it took a few minutes to get the Hilton welcome page to show up, but so far I haven't had any problems on the road.
And I had the same frustrations with Google maps, but today I noticed that if I just type a location into Google as a regular search (e.g. "Trader Joe's downtown Chicago") then Google gives me its own generic info about it, and one of the options is to click on Map. I didn't have any high hopes, but I clicked and I actually got a real, readable map! Of course, it did crash when I then clicked on "Directions", but it's a start.
I'm very interested to hear your successes with the Mifi. We're going to be all over the globe in the next few months, and I should seriously think about that as a solution.
Thanks again!