@Phi***
, You could do that but here's another idea.
When you're back in the US, apply for a year-long, multi-entry Non-Immigrant Type O-A (Long Stay) visa from either Chicago, LA, New York or Washington DC (the only places that sell them now).
It does take a background check and a medical certificate But you can show the proof of finances in your account in the US.
That visa is good for unlimited entries for the validity of the visa itself (one year from the date it's issued) and every time you enter thailand you get stamped in for a completely NEW calendar year.