I'm moving to the Philippines at the end of November. I'll be staying in Tagaytay at first, and then I plan to explore other areas.

Get the Wise Transfer and Western Union mobile apps. You can link them to your home country bank and send money from there. Unless you need it for a long-term visa, you don't need a Philippine bank account. Mint Mobile and Tello are affordable plans for keeping your home country phone number. For local calls and data, just use a local SIM like Globe. Don't rent for more than 3 to 6 months at a time so you can experience different areas of the Philippines. Airbnb works well for that. For a base, I recommend Iloilo City and Bacolod City. They have decent infrastructure with everything you need, and the airports are good.

My wife (she's Filipino) and I are also thinking about moving to Tagaytay. We'll look for a suitable house in January. Tagaytay is the only place where the weather is bearable for me. The house prices also seem reasonable.

Don't cut all ties with the US. Keep a US phone number and use WiFi mode! Buy a dual SIM phone or a cheap phone for a Philippine number! If possible, keep a US address too, like at a friend's or family member's house! The weather in Tagaytay will be to your liking! Have a safe trip!