TeleWork Noob; Looking for Tips

Hello, I'm new to the telework world, and I'm looking to maximize the opportunity. I'm looking for a short of "how to" guide to getting the most out of being able to telework and travel. Below are some general questions, but not a full list.

1. Staying within the US time zone is important so which countries would be best. Cost is not a major factor.
2. What is the best option for short term stays?
3. Is google flights the best travel site for flights?
4. What travel sites do digital nomads use for places to stay, flights, and public transit?

Thanks for reading