First of all, Wise has a $200k transfer limit. 2nd, transfers and holding money in your wise account are 2 different things. 3rd, yes there's tons of people have have their accounts frozen and lose their money, join the Wise FB group.
Non-OA is a multiple entry visa. "Reentry stamps" are only for single entry visas... Also, for the Non-OA you only get stamped in the as long as your insurance is valid for. If you reenter Thailand with 1 year insruance before the OA expires, you'll be stamped in for another yera.