If you don't want your US banks to tell you that you need to close your bank accounts (your US credit cards would be next) you need to keep a physical US home address on your bank profiles. Family/friend address would take satisfy this. Setting everything to electronic minimizes postal mail and you could sign up for a mail service for any limited physical mail. These services are cheap ($120/yr) and offer opening and scanning mail pieces for small extra fees. These services CANNOT be used for home addresses.
The blame would be with your airline (*ie. your responsibility) therefore, Immigration is not going to ignore an overstay. You'd need to apply for an extension or contact your airline to change to a different flight on an earlier date within your 60 days. Your airline should not charge you for that change.
The only possibility for an issue is at initial check when you're departing but even that is unlikely since you have a return flight booked. They should be aware of the 30 day extension option or multiple other options available (exit/reenter Thailand to other countries as part of your trip). Almost zero chance of a problem but in the
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,000 chance, the onward ticket sites offer temp tickets for $20-$25. I'd bet no problems tho.
Agreed AIS. Prepaid plans are cheap and offered for tourists but if you are going to live there, they offer even cheaper post-pay plans that are great. You just need to show them proof of a long term visa (ex. retirement visa) and you pay monthly.
Been there. Stayed in Cebu for over 2 weeks, few days in Manila and surrounding area. Accommodation costs were about 3-4x higher than in Thailand for poorer quality accommodations.