So I got here in August, on a double entry tourist visa. Extended my first stay went to Hong Kong and got my second entry at the airport. My visa expires Dec 14 and I am going to immigration next week to get the thirty day extension. That gives me till mid January. Problem is, I will be traveling with my family for most of early January, will I be able to go to Mae Sai and do a quick one day visa run, and then get another tourist visa in February, probably in KL? Or will the entries and extensions mess up my chances? Do I need to go get another visa in January? In other words, can I have had the tourist visa, do one visa exempt and then get another tourist visa?!

Thanks

As the rules are understood today (max 90 days in any 180 day period on visa-exempt stamps) you should be fine, as your stay is based (mostly) on tourist visas. Cheers!