I've done something similar with Deel for a couple years, hopping between Portugal, Spain, and Estonia (all EU for smoother transitions). Stays were 4-6 months each, same time zone-ish. HR was cool after I pitched it as low-risk continuity-no termination needed, just a location update in their system. Deel handled the switch in 2-4 weeks, mostly needing updated address proof, passport copy, and sometimes a local bank statement for KYC. No police checks or diplomas for me.
Big gotcha: Taxes. Without totalization agreements, you might double-dip social contributions short-term, but I got refunds via end-of-year filings. Frame PE risk to Legal by emphasizing you're not establishing a fixed base-just transient WFH. For insurance, I stuck with my global Cigna plan and opted out of local EOR coverage to avoid overlaps.
Costs: Company covered the ~$50-100 switch fees as it kept me productive. Sanity check: Totally viable if your EOR supports it (ask yours directly), but test with one move first. Don't hop to non-treaty countries like Thailand without DN visa-payroll gets dicey on tourist stays.