Sorry this is going to be a bit of a long post. I've been telecommuting full time more or less since January (with a few month long stops to the physical office in DC) and right now I'm trying to find a good location to spend a month or so working remotely in the October-November timeframe. I have to more or less keep East Coast US hours (10-4 availability) and I have to be fully connected, internet and phone, M-F, 40 hours a week.
Right now my ideal location would be something with very reliable internet, in a city with good night life and a beach, where I can find a 1 br apartment on airbnb for under $1500 for a single month(less is better, but that would be my DC rent so that's my cap).
In the last 6 months I've tried a lot of cities but haven't found any that really fit. I've tried: Medellin (I did like the city, the weather, and the people but i'd like something with a beach), Cartagena (seems to meet my criteria but locals there seemed really jaded by tourists and seemed to just be trying to rip everyone off), Bogota (fun for a bit but doesn't hit any of what i'm looking for), Quito (felt really unsafe), Puerto Vallarta (Beautiful place and met a lot of the criteria but I found it hard to make friends with locals and the tourists were mostly retirees), Buenos Aires (really liked the city and would spend more time there but I'd like something with a beach), Madrid (I used to live there so I used it as a test run for trying to work with a large time difference and it didn't go super well), also did brief visits to Santa Marta, and Montevideo, and I've been to Santiago and Vina del mar before.
I have flight benefits through my family, so it would be awesome if anyone had recommendations for the following cities or places nearby: Aruba, Belize City, Bogotá, Buenos Aires–Ezeiza, Cancún, Cozumel, Grand Cayman, Guadalajara, Guatemala City, Liberia, Lima, Managua, Mérida, Mexico City, Montego Bay, Nassau, Panama City, Port of Spain, Puerto Vallarta, Punta Cana, Quito, Rio de Janeiro–Galeão, Roatán, San José de Costa Rica, San José del Cabo, San Juan, San Pedro Sula, San Salvador, Santiago de Chile, São Paulo–Guarulhos, Tegucigalpa.
From those locations I felt like most of the Caribbean is probably mostly expensive resorts and the internet may not be great, so I've mostly been looking at Central/South America or Mexico. I speak conversational spanish more or less so my preference would be somewhere Spanish or a place where its easy to get by with English.
I'd really appreciate any advice people can give.