Seems like a wealth of diverse views here. I read the threads started by @KellyCannon, @MDGringo, and @Emmanuel01 with great interest.
We're planning our "Do we really want to relocate to Santiago?" reconnaissance mission Jan 23-Feb. 12. We seek advice generally on what to check out while we're there. But since this forum seems to have lots of helpful perspectives, I'll just lay out what we seek and why we think we may want to move to Santiago.
I'm a retired American entrepreneur. Moved out of what's left of the USA in 2009 and have zero interest in ever going back except to visit.
I'm a city-dweller at heart. Love Manhattan but hate cold weather. So my first expat adventure was two amazing years in Hong Kong. Loved the food and the city life but eventually realized I was paying for the most expensive real estate on the face of the earth and had no real need to be there other than the Dim Sum.
After HK my ex and I took a trip around the world, "test driving" what living in 28 different cities around the world felt like. Santiago (we spent 3 weeks there in Dec. 2011) was a curious one because on one hand the food was awesome (food is very important to me) and it just seemed like a cool city. But at the time I spoke ZERO Spanish and Chile is very unforgiving of gringos who can't count to 10 in Spanish. The result was a mixed experience - didn't especially love the visit, but walked away with a strong impression that it would have been much, much different had I been fluent.
After the big trip I concluded that continuing the travel lifestyle was the thing to do, but I needed a home base much cheaper than Hong Kong, so I could leave the house empty for months at a time while traveling and not care about the rent.
It's hard to do better than Mexico when it comes to a CHEAP home base. Spent a couple of winters in Puerto Vallarta, but quickly tired of living in a tourist town. And the restaurants sucked royally.
Would have left Mexico, but by then I had a new girlfriend, Russian, whose passport isn't as versatile as mine. We couldn't stomach any more Vallarta, and were surprised how much we've enjoyed Guadalajara, which offers convenient flights to everywhere and everything is dirt cheap. We've lived here just over a year.
But my girl never wants to give up her Russian passport, and Mexico doesn't allow dual citizenship, so naturalization here is not an option.
Reasons we THINK Santiago might be next:
* 4,000+ Restaurants as opposed to <1,000 in Guadalajara. Food is very important to us, and I remember some amazing Ceviches and other fare in Santiago from my 2011 visit.
* Appears to be the only "real city" in Chile. (I consider places like Boston and San Francisco to be too small to be interesting and I call them pseudo-cities, as a point of reference).
* Process of obtaining permanent residency then naturalization seems well within reach for both of us, without losing existing passports.
* Naturalization option after 5 years would give both of us a 2nd passport and broaden our visa-free travel options considerably.
* There are almost no educated, professionals who speak English here in Guadalajara. We have essentially no circle of friends. Our impression is that there is at least a small English-speaking expat community in Santiago.
* There is Uber service there (We are addicted to Uber in Mexico and never use the car we own because Uber is so much more convenient).
* Believe it or not, we speak 'solo un poquito' because we can't find a maestra/masetro de Espanol willing to come to our home to teach us Spanish! This service is readily available in the tourist areas of Mexico but not in cities like GDL. We've met several English teachers from local universities and offered to pay them handsomely to come ot our home, but they're too lazy to want the work. Just one of many frustrating oddities of Mexican culture.
Reasons we're hesitant about Santiago:
* Miserable weather. We're spolied beyond belief. We think Guadalajara is way too cold because it occasionally dips below 10C in the dead of winter here. We would have to leave Chile for Jun-Jul-Aug bare minimum - we just plain don't do cold weather. We can afford to travel, but know from experience this adds considerable complexity. It means we have to live in a condo or gated community with security so we can leave the house empty for months at a time. I've lived this way before and know the downsides...
* Everything appears to cost at least DOUBLE what it would in Mexico, especially real estate. To some extent you get what you pay for, I suppose, but the 7,000sf home we live in here would definitely be unaffordable there.
* Long flight to just about everywhere. I've spent enough time in Argentina to know I never want to go back for the rest of my life. Brazil would be a great trip if it were not rapidly devolving into social chaos. The food sucks in Columbia. So to get out of Chile would mean Europe or USA, both very long flights.
* Despite being one of the best naturalization programs around, the fact remains that 6 yrs to get the passport is still a long time. Would we last that long before we got sick of the miserable winters?
OUR REQUEST OF THIS COMMUNITY:
Based on the above description of our goals and assumptions/beliefs about Santiago, what do you guys think? Are we on the right track, or are we barking up the wrong tree?
Also, is there anything in particular we should be checking out when we're in town for 3 weeks in Jan/Feb?
Are our assumptions wrong? In particular, I assume there is no better place for us in Chile than Santiago, simply because we're city dwellers and cherish a LARGE selection of really great restaurants. I know there are warmer places, but they look tiny. Remember, I'm the kind of person who thinks San Francisco is a sleepy little town masqurading as a real city... So small towns are not for us, even if they're naturally beautiful.
Thanks in advance!
Erik