I've been "hotel homeless"/"digital nomad"/whatever since April of this year, and it's pretty great so far. I find the key is to find cheap places you can stay for a week or two in-between (and close to) the places you bounce between.
For example, I am in SF, Chicago, and NYC a lot. I have a super cheap place in Detroit (my hometown) where I can go when I just need to work for a week or two in between 5-10 day trips to the coasts or Chicago. Same goes for Europe - it's cheap to stay in Berlin for two weeks, not so much in London. I buy one-way tickets so I don't have to decide in advance how long I want to stay in a place.
Good luck with your visa @onceuponatime, it will be great to see you again at the second annual. :)
How do you get around the 3 month EU limitation?
Bounce out of eu to turkey or north africa and get another visa, Ireland is the best one or UK to get travel visa for US or Canadian citizens, then you can travel on from there. Actually you could probably just go to Switzerland or Norway too as they are not part of eu. Good luck with travels. I just realised that there is the 6 month wait in between visas, get a travel work visa in Ireland as I think theyre pretty relaxed.
Switzerland and Norway are both part of the Schengen treaty area and enforce the same 3 month visa and 6 month in between visas with the EU countries.
I spend less than 50% of my time in the Schengen Area, and never more than 85-89 days at a time.
I used to have a German residence permit, though.