I've noticed since many other countries stopped stamping passports, my passport has become dominated by Thailand stamps, which seems to trigger the border officers' suspicions - hence, if you come often but never stay for a long and spend most of your time elsewhere, it might be worth summarising your travel history on a separate piece of paper to make it easier for the border officers to understand
no limit, but if your travel history suggests you may be living in Thailand, rather than being a genuine tourist, you will eventually be asked questions and then, depending on how satisfied they are with your answers, either told to get a visa or denied entry
I know a Thai who did this as the seller, but only because nobody wanted to buy the property outright. You're setting yourself up to get hurt by adverse selection.
he should get that checked ASAP - a few years ago I got stamped for 60 days instead of 30 days due to a mistake by the staff at that same border - as a result I overstayed by 30 days and Bangkok immigration couldn't make allowances.
You can do tourist exemptions / tourist visas until they pull you up on it, then you'll either need to buy an Elite visa or incorporate your business here and get a visa through that (I think this would be the best option as it means you can still legally manage your business even when you're here).
With regard to living costs, it depends more on your spending habits than anything else.
No specific limit as long as your travel history doesn't suggest you're using tourist visas / exemptions to live in Thailand - i.e. if you're consistently spending more than half your time in Thailand