it depends on your skill set. i don't take a discount on my rate because i'm outside the country. someone who is fine making $30k a year for the same job is probably going to suck at it. been there, had to fix that.
the number of things i've had to fix/fires i've had to put out from companies skimping on their staff because they want to be cheap is crazy and almost always cost them more in then end than just paying fairly would have cost.
yes, it's possible if you have the experience to sell it. and you should research FEIE as the savings there can be huge.
nope. you just have to go at the right time and negotiate. i've rented a beautiful one bedroom a couple blocks from the sea with a huge terrace and amazing kitchen for sub $600/month for this winter in greece. booked it last week.
you should have a real onward ticket for when your visa expires. you'll have the expiration date so just leave that day or the day before.
don't go to major cities. that will help a lot. but yeah, the answers are get creative and try alternative housing or suck up the prices. but there are deals to be had if you go to non major cities and travel off season.
Different countries have different rules. and not just the US have bilateral agreements.
you should still be tracking manually. and don't trust apps.
is there a reason you can't just follow the law? zone hopping is not difficult. i've been doing it in europe for the last 10 years. i've never overstayed or needed to.
you stay in tokyo until you get a visa or you go elsewhere.
i don't see your pets mentioned in any of your options. you chose to be responsible for them until they die. so you need to figure out how to give them a good stable life, then you can figure out how that can be best as possible for you.
yeah, that's either going to be ridiculously expensive (global esim) or not possible. i've been on the road full time for 15 years. i've just accepted that i need to get a new sim every time i move. it's not that big of a deal.
there are US plans that allow roaming but they'll cut you off after a while.
i'd stay literally anywhere but medellin. in 15 years of nomading it's the only place i'll never return to.