Is there a good resource for what types of work and for what duration might trigger any sorts of obligations for the company? Some states do not have clear guidelines for employment taxes, and looking at other countries is an even more mixed bag. It doesn't have to be exhaustive, but even pointers to each state's or country's resources (if available) would be useful.
Example scenarios that I'd like to have information on:
1. An employee in Colorado is visiting family in Pennsylvania for the holidays. The employee is flying out a week early and plans to work remotely for five days. The company is headquartered in California and has no other employees or offices in Pennsylvania.
2. The company is holding sales kickoff in Tennessee for five days. An employee in Maine wants to get out of winter early and spend a month renting a house in Tennessee around the offsite, staying a few weeks before and a week after. The company is willing to cover the cost of the rental during the week of the offsite, but the employee is paying the rest of the cost.
3. An employee in Utah likes to work around ski season. They want to spend as much time as they can in Chile over the southern hemisphere winter. Outside of employee visa issues, what should the company be aware of in the cases of contracts or other matters?
A lot of this often gets glossed over in smaller companies (and sometimes larger ones), and maybe that's the right way to look at it. I only know of one other company that keeps a red/yellow/green list of places to work nomadicly, and that's due to the nature of their deals, contract sizes, and traveling workforce.
Other than having an employment lawyer look into each detailed scenario, can I answer basic questions around duration of nomadic remote work that warrants further investigation?