Considering a move to Chile

I’m 62 recently retired American (USA) considering Chile as place to live. Currently in Santiago (Providencia) for a visit. Will visit Vina Del Mar / Valparaiso as well. Based on some scouting of different countries will narrow list and spend more time on ground before making the move.

• Any expat meet ups in next few days? Would love to meet others who have made a similar move. Open to 1:1 dialogue as well.
• Pros / cons of other Central / South American countries, in particular Uruguay, Colombia, Panama
• I will need to learn Spanish. Any tutor / school recommendations? Level of difficulty getting by with English as I learn basic Spanish?
• Any recommendations of relocation agents?
• On Friday I head to the coast, with luggage. Intend to take bus. Any tips?

thanks much for your information in advance.