I've been considering an arrangement like this too, only I've heard a number of stories about people who kept taking "weekend" trips to renew their 90 day visas

I've been considering an arrangement like this too, only I've heard a number of stories about people who kept taking "weekend" trips to renew their 90 day visas only to one day not be able to re-enter the country. I've overstayed an EU visa and no one seemed to care (I was traveling so much between EU countries that I honestly wasn't even thinking about it) but if you overstay somewhere like Singapore you can literally get caned. I'd look into countries where there are easier ways to get >90 day tourist visas, like Cambodia or Hong Kong.