Yeah, this is accepting some digital nomad hacks (Florida as your “home” state [or another no income tax state like TN or SD], skating by on tourist visas when traveling, hence the 90 days stipulation) until digital nomad acceptance increases (~46 countries are issuing visas to nomads who have a remote gig from a quick web search).

(not an endorsement of any specific legal or immigration actions)

r/digitalnomads has some interesting data points on people's IPs and VPNs being flagged as "outside the US".

You’ll definitely want to get ground truth from your org if you should be routing through a friendly residential connection in your org’s jurisdiction while traveling.