Hi Duke,
Great to read a bit of your life story. I am actually trying to start my career in the Airlines but moved to South America in order to do it cheaper and quicker (quicker part has not materialized yet!)
I have been in Chile for the past 5+ years and have bought an apartment in Santiago along with around an acre and a half of land in the South of Chile. The land itself cost around US$6.000 but as I am only looking at it as an investment you would obviously have to scope out what sort of farming you can do in different areas. Similar to New Zealand a lot of Americans are coming down to buy land (check out Douglas Tompkins the North Face founder RIP) and Kingston Vineyard owned by an American-Chilean family
https://www.kingstonvineyards.com/About/History who admittedly arrived a long time ago! There are a lot of other examples but wanted to show you a couple.
Why am I plugging Chile? Compared to Argentina the economy has been doing well ever since the 1970s. The country loves foreigners (as long as you don't constantly complain about what is better in the US you would be fine - god those people are annoying.)
Now the major pain in the butt part, bureaucracy. You can start your visa application but it will take roughly around 1 year to be approved - I am not a visa expert but I think with a certain level of money you are bringing into the country you would be able to get one. In the meantime every 90 days you have to do a quick visa run to Argentina or Peru with flights being around US$100-200 so not breaking the bank. Currently immigration is dealing with large numbers of Venezuelans and Haitians coming for a better life but literally arriving with nothing to their name so you would be in a good position.
Taking advantage of the Venezuelan issue, you have some of the best looking women in the world coming to Chile for work and security, i'm sure you'd be doing well with them if you can offer them one of those two aspects! Now to cover an important part, if you wanted to get married in Chile there are 2 ways to go about this. 1. Half of what is yours is your spouses if you divorce (I know no-one that has gone this route) 2. Whatever you came into the marriage with cannot be given to your spouse but anything accumulated afterwards is split 50/50. Kind of a little more attractive than getting completely destroyed in a US divorce court and hence why I have bought my stuff whilst still being single.
Flight time and time zone as you are probably aware is around 8-10 hours depending on which state you are visiting and currently EST time is the same as Santiago and 1-2 hours difference in US winter/Chilean summer.
Chileans are always interested in foreigners that move to Chile and very proud of their country and you will make friends quickly depending on how sociable you are along with the fact you can speak Spanish (Chilean Spanish is very very different to other countries so don't be too shocked with that.)
Final point is the schooling side for your grandson. There are a bunch of excellent private schools in Santiago and spread out amongst other cities in Chile (obviously Santiago has the best) these have British and American heritage to name a few:
The Grange (UK)
Craighouse (UK)
Nido de Aguila (US)
Santiago College (US)
Will leave this link here for you to do your own research
http://www.expat-quotes.com/guides/chile...-chile.htm
I have been to SE Asia and loved it but home for me is now South America and have visited every country apart from Venezuela in the region. Argentina is great but politically run poorly. Colombia had a bad reputation but now is doing extremely well, Panama and Costa Rica both attract a bunch of US expats. Peru is developing quickly but if I could do it again i'd chose Chile without a doubt.
I highly recommend you use some of those airline tickets you get and check out both Argentina and Chile to make an informed decision as well as any other countries you are interested in.
If you want more info or are coming down don't hesitate to PM me.
Good luck!