You're probably giving too much information. I always just say I have an agency and work with clients around the world online.
I have gotten zero negativity with this story.
You don't get extra points for telling more than you need to. Less is definitely more.
Plus it has the added benefit of giving people zero information about how much you make.
Please read the VPN wiki
Yep, turns out tons of other people are willing to pay the high prices.
The best option is avoiding the family / kids and just plowing (dating) for decades.
Depends on the country.
Countries in LATAM have very weak enforcement, so if you keep your mouth shut, you won't have to pay taxes.
Usually just following Don't Ask, Don't tell avoids any issues on countries where enforcement is weak. Just talk with the locals about taxes and you can get a general sense.
I highly recommend working with a local lawyer the verify what the rules are, and what risks you are taking.
I'd say KFC in Pyongyang is probably the furthest I've been. 1500 KPW for a meal is a steal.
+1 for US mobile. Been doing this for almost a year, and, so far, works like a charm.
You have to start with the end goal in mind.
Look at careers that are remote friendly, decide which ones appeal to you, and then move in that direction.
If you choose wrong up front, and there are definitely wrong choices, it will make it a lot harder on the backend.