A Schengen passport get you access to the entire EU. So you can buy an apartment in one country, and then just rent it out later. No guarantee you get you money back, but you'll get some return.
I strongly recommend the lifestyle. I loved northern Italy. Walking, biking, cycling everywhere. I eventually realized a car didn't matter, and not having a car was a point of pride. Live in the Centro Storico. I had three grocery stores in walking distance. It was lovely.
Taxes are an issue, but it can be dealt with. Medical isn't really too bad, you won't be comfortable until you get there and do it. Don't let it stand in the way. Consider doing 90 days in an AirBnB just to get used to living there and evaluate you options for a permanent location.
It's worth noting that living costs are probably 1/3 cheaper in most places, like Italy or France.
If I am able to get it done, I will be in either Paris, the French Riviera, or northern Italy. The way my bitcoin is seemingly going it's just a matter of time. But who knows really.