If I can get the back-to-back visa exempt stamp than it seems way easier than getting a visa. 2 runs are more than enough for me, probably even one and I can extend that. Just wasn't sure if I can get it. Thanks for all the replies!
So is this ok now? I've purchased the "Nomad Guide Chiang Mai" PDF and it specifically says that back-to-back visa exempt entries are not granted anymore (mentioning Mae Sai in particular). The info in this PDF is probably about 2 years old though, did they relax these rules since?