A few yers ago I looked into the Digital Nomad thing. Realistically I'm unlikely to persue it due to family. But if you can make it work then it's worth a try. As for the monitor what a lot of people do is either take a portable 15" monitor as a second screen or, if you need something larger, just buy a cheap old monitor from ebay or facebook marketplace when you arrive and then sell it again when you leave.
I might look into it a bit more. My monitor will actually fit into hold luggage if I could pack it safely.
The main issue I could see would be getting suitable accommodation at a decent price. Short term rental in the 3-6 month range is a bit niche but I suppose demand is increasing these days for the digital nomad life.