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We've been in Argentina for 2 and half years now, with a few trips in that time.
My favorites are Brazil > Colombia > Argentina (only because of Buenos Aires, the city - not the people).
I love Brazil and Brazilians are my favorite people in South America. If not for safety concerns, Brazil would have been our base. We've spent 1 year there. I've also spent 1 year total in Colombia, over a few stays. Colombia is fun and Colombians are cool, but like Brazil, safety is a concern. When it was just me, it was fine, but with a family, I'm playing it safer.
If you don't want to deal with longer term visa issues, Argentina is your best option. They have the most relaxed immigration system I know of. It's one of the few countries where overstaying your tourist visa is not "illegal" or even frowned upon (except you do it too many times). You are legally allowed to overstay up to 4 years. Yes, 4 years. You just have to pay a small fee on exit. That fee remains the same, whether you overstay by 1 day or by 4 years.
Last time I paid the fee was a few months ago, as I had business to take care of back in the US, the fee was... $12. Used to be a lot more expensive, but inflation has crippled the Argentine Peso. I paid it, left, and returned less than 2 weeks later. I've only paid the overstay fee twice. Immigration officers will advice you to overstay, if for instance, you've done a visa extension and aren't eligible for a second one at that time. They've told me to overstay two times, so far. You are more likely to be given a hard time for doing a visa run than overstaying, although that almost never happens either.
We now have automatic permanent residency and are eligible to apply for citizenship, based on having our baby here. I haven't decided if I want the citizenship, but the permanent residency is nice.
My least favorite place was Costa Rica. Spent 3 months in San Jose. Overpriced and lower quality city with very little interesting things to do, so poor value for money. Highlight of our stay in Costa Rica was a trip to Manuel Antonio for some days. Great rain forest hikes, nice beaches and ATV rides through the rural paths. Many American retirees love Costa Rica, but it's not for me, and I'm still far from traditional retirement age. I'd recommend spending about 3 months in several countries, then decide which one is more your speed.
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