if you have a social security account, they will provide you with a letter of income. It took a while for me to figure it out. Thai immigration accepted the letter and it is easily updated.
There's a lot of women here in Thailand. It can be difficult to find a man that will care and support them. Many are good companions. I would suggest you find one with a real job to insure she isn't looking for the easy way out. I've seen many men taken advantage of here and fewer who found their soulmate. Do your research.
I made a couple of runs out of Phuket last year. They really drive fast. Then I flew to Kuala Lumpur. Hard to say which was scarier. Now I drive my Honda Click to Cambodia. It's only an hour each way and the roads are safe.
I think it all depends on where you start. And you might regret not bringing a helmet no matter how you decide to travel.
I do it in multiple deposits. The bank statements verify. It's not a problem at my immigration office. Every office seems to have different requirements.