saddlesores

if over 50, you can get a "retirement" visa in thailand. minimal requirements, but not allowed to work. you'd need to have a source of income. digital nomading is possible if you keep a low profile. can work in a third country part-time, no tax paid to thailand or usa.

if collecting social security, no problems, can easily live off less than $500/month. you can get an efficiency apartment in bangkok for $75, healthcare 1/4 the price in the usa. health insurance under $1k/year and no obamacare.

set up as a base for traveling throughout the region with no winter. buses, trains and cheap flights to interesting places.

touring in the region should run $20-25/day staying in guesthouses, cheaper if you feel like camping.

also possible to set up in vietnam, cambodia or laos with various types of visas. malaysia and indonesia have real retirement visas, but with higher requirements.

i've heard Philippines is even easier if you're a us citizen.