Looking to relocate. But to where?

I’m sure your’re right. Alas, Buenos Aires is located in an appealing time zone.

Why alas? No matter what it's going to be substantially cheaper than Boston. Buenos Aires used to be referred to as the "Paris" of South America in the roaring 1920s. Has the best architecture in South America and if you choose you can live very frugally. There are neighborhoods much, much cheaper than Palermo and it has a more civilized atmosphere than Cuenca or Lake Atitlan.
Palermo is only second to Recoleta in my view. Recoleta is like Beacon Hill of Boston IE upscale.
 
Why alas? No matter what it's going to be substantially cheaper than Boston. Buenos Aires used to be referred to as the "Paris" of South America in the roaring 1920s. Has the best architecture in South America and if you choose you can live very frugally. There are neighborhoods much, much cheaper than Palermo and it has a more civilized atmosphere than Cuenca or Lake Atitlan.
Palermo is only second to Recoleta in my view. Recoleta is like Beacon Hill of Boston IE upscale.
“Alas” because Argentina is nutso, isn’t it?
 
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What is your opinion of Cebu? Where are the safe places in the Philippines?

I lived in manila and played poker years ago. Didn't trade. How much is fiber optics in Manila / Cebu?

Philippines is safe for Americans I heard, bc of the US / Philippines foreign aid. They don't kidnap Americans in general. There's also lotsa women that'll probably love you. The place is cheap, Rent is more than 400 USD in manila more like 600-800 in safe areas. It's a good place I lived there for like 6 months. Bars and food and culture is very american. The locals like foreigners.
 
I've heard the traffic in Metro Manila is gridlocked to the point of absurdity, is that hyperbole or does it really impact your ability to live there?
Irrelevant. You only go out at night, the place is so hot in the morning. It's before 10 a.m. and after 8 p.m. that you'd wanna be outside. If you live downtown financial district, you're 5 minutes drive to the nicest mall in the world, IMO.
 
The kids are growing up and I'm seeing less and less reason to live where I live (outside of Boston, in one of the most expensive zip codes on earth.) So I'm looking to relocate to someplace that imposes less of an overhead.

Factors to consider...

1) low cost of living
2) high quality of life
3) reliable internet infrastructure
4) time zone no "worse" than central time, USA (rules out anything west of GMT -5:00)
5) not hot (I'm a New Englander)

I'm intrigued by Latin America (highlands, obviously, for temperature's sake) and Eastern Europe (culture, time zone).

Any thoughts? Anyone?
If you like smaller city colonial style..cool weather...decent cable internet...coffee shops...etc then check out San Cristobal De Las Casas in the highlands of southern Mexico. I lived there for years. Just never could adapt well to the altitude. And the cold. But you would probally like its weather. It has Sams Club..medium size mall..theaters...and of course Mcdonalds..Burger King etc along with many local food restaurants. If you need bigger city style then Tuxtla Gutierrez is just about 30 minutes away. But it is a warmer climate. Both places have great coffee shops and in the evenings the central park is usually full of people meandering around ...relaxing..drinking coffee...and at times performers entertaining. Cost of living isn't too bad. In San Cristobal one can rent a decent house in a decent gated neighborhood for 500 to 800 dollars a month. I think i paid about 200 or 300 in a gated community but that was a few years back. I have friends who live there. Lots of tourists come there ....mostly Europeans. Biggest downside is nothing to do much after you check out all the historical sites. You can travel about 1 hour away to the lagos de montebello or find things to do in Tuxtla Guitierrez but if you just wanna go relax..trade the markets...sit around.. drink coffee...wind down...well this might work for you. Tuxtla has an airport to travel to USA via Mexico City.

Lots of Taxis and little buses running aroubd San Cristobal so you actually don't even need a car. However, you can take a car down and get 6 months permit. Then you drive a couple hours to Guatemala ..leave Mexico stay a couple nights in Guatemala and come back in to Mexico for another 6 months.

Google and check it out:

San Cristobal de las Casas, Chiapas, Mexico
 
For example: here is a smaller house fully furnished with cable and internet and probally utilities too for 700 dollars a month. I think it is in or very near to the last gated community I lived in. Quiet neighborhood on the edge of town. These sorts of place abound there. You can rent bigger homes also. However, buying a home is quite expensive if in a gated community. Don't know if you looking to rent or buy. People come and stay months or years in these sort of places.

If you are a big party animal San Cristobal is not for you. Check out the reviews...Like I said many places similiar to this abound. Some downtown.

https://www.airbnb.com/rooms/892299
 
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Ford???


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And me without my towel.....


[by-the-way.... R.I.P., Marvin The Paranoid Android.... what a great actor, whether voice-talent or live.]
I don't know what it is about this picture.... but for some reason every time I see it.... it reminds of the elevators in Trump Tower.
 
You did not list any time zone limitations east of central time, so I will assume that you want to stay roughly close to the USA east coast time for trading purposes. That rules out all of Europe, Asia and Australia, unless you want to be trading in the middle of the night.

In the USA, I would consider San Diego, it fits all your criteria, except for the Time Zone. Best weather in the USA.

In Latin America, San Jose, Costa Rica would be a great choice. Best weather in the western hemisphere (average temperature in summer 68 degrees, average in winter 63 degrees), low crime rate, decent medical facilities (2nd longest life span in the western hemisphere after Canada), and one of the few countries in Latin America where you won't have any problems finding people who can speak English.

I live in San Diego and it has the best climate - 70 degrees in winter is nothing to sneeze at. Bear in mind however that the cost of living here is not cheap, with the price of a three bedroom house in the $600's for a reasonably decent area. I've met some people who have decided to go south and live just across the border in Mexico. They say it is mostly crime free and can live a great life on a fraction of what it costs to live north of the border. Additionally some even commute to San Deigo every day. PLus the climate is the same.
 
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