Trainaway.fit is probably the closest thing to what you mentioned, as they cover many countries. However, they only sell day passes. I used them a few years ago. Source: almost 2 years ago

For example I didn't know about https://nomadlist.com or that some countries are doing work visas specifically targeted towards digital nomads or how taxation works. - Source: Hacker News / about 2 months ago

As a digital nomad, you can work wherever you want provided you have access to an internet connection. If you're interested, this is a good website to start learning about it: https://nomadlist.com/. Source: 12 months ago

Here's a good place to start https://nomadlist.com. Source: 12 months ago

I understand that year-round weather might be important factor for you. But I would still say that the fundament of nomad lifestyle (both historical and current) is following important patterns (of weather, animals, prices, interests...), so whether somewhere one of this factor is stable (year-round) is not so important when you are nomad, as you can harmonise your changing places with the change of these... Source: 12 months ago

Nomadlist.com (reviews of countries, cities) + its discussion groups on Slack for individual countries etc. (when you are paid member). Source: 12 months ago