@Ryan ***
. There is actually only one thing which is frowned upon and that is not having the correct visa for your intention to be in Thailand. Yes, they get shitty with people who think they are smart by using a variety of methods to circumnavigate their system. If you follow their rules you should have no problem, although you can always strike one cranky IO who got out of bed the wrong side. Doing a land border crossing carries less risk as
@T**
has said. Worse case scenario if you are refused entry, better to be sent back into Laos etc, than be detained at an airport and sent back to country of origin