You realize that 1) insurance coverage is not required for non-o based on retirement visa. 2) healthcare is at least ⅓ the cost of haha in USA and its in many ways better quality.
Suggest you get retirement visa while abroad. Makes whole process much easier. Maintain USA bank and investment accounts and transfer money as needed. Your money will earn a lot more there than here and it is much safer. Suggest retirement versus marriage. Less paperwork and lower risk if for some reason your marriage didn't work out in the future.