Slow travel advice Southeast Asia

Hey,

I’m getting ready to do an extended slow travel in Southeast Asia, planning to stay the maximum duration without applying for a visa in Cambodia, Indonesia (Bali), Malaysia (KL), Philippines (Makati), Thailand (Phuket), Vietnam (Da Nang). Goal is to emulate an actual retirement lifestyle and see where I enjoy life, so I wanted to ask advice from more experienced travelers on what they wish they knew accounted for before these trips

Where are some good places to stay when I’m traveling? I’ve heard people say I should look on Facebook for deals?

I’m guessing I should not be out wearing designer even if the city is safe in a developing nation?

What’s the best way to engage with the expat community and make friends, business contacts, and otherwise network?

Where did you get your health insurance?