Brazil was (really) very expensive, possibly higher than Boston. So, don't recommend it as a cheap away location unless you have a good lodging option. If you can find good internet, Managua in Nicaragua is a fun city with lots of beaches, volcanoes, and old cities to explore on the weekends.
If you want something logistically easy, the Yucatan in Mexico has tons of options and is relatively cheap. Tulum is not too crowded, lodges have good internet in the commons areas.
Dimagi didn't pay for anything in this case, it was all self funded by the individuals on the trip. But I think they would all agree it was money very well spent.
Most of the dev team works a very flexible 40 hrs. Some of the more senior folks work a bit more but its all because we want to. It would likely have been too much if we were pulling 60 hr work weeks.
If you want something logistically easy, the Yucatan in Mexico has tons of options and is relatively cheap. Tulum is not too crowded, lodges have good internet in the commons areas.