Initial entry at a land border with a brand new passport with no previous thatland stamps makes you look like a criminal who's afraid of being arrested if you flew in.
if you fill out a tax form for the business and it makes 40k to 80k a year in taxable profit. Otherwise just go there and sign up for a 3 month or 6 months soft power course
I did exactly what you are describing. I stayed in Thailand for 60 days introducing myself to a few ladies, then visited a few countries for 14 days with my instant love girlfriend, then came back to Thailand. They looked through all my stamps to see where I went and stamped me back in for 60 more
You can't live in Thailand all year and not pay them a boat load of cash. You can split your time between Thailand, Malaysia, Korea, and Philippines and not have to cough up too much cash and have a warm and sweet girlfriend in each one to take care of your laundry, cooking, and entertainment