Why not. There's plenty of more detailed info out there, and I don't claim to be any sort of expert after mere two years, but here's two stereotypical extremes:
Tourist-eyes: beautiful beaches; nice weather; safe; cheap food; laid back, friendly smiling people -- PARADISE!
Live-and-work-there-eyes: rampant bigotry and racism (common to most SE Asia); dishonesty ("losing face" and all, again shared across SEA and not specific to Thailand); nothing ever gets done (the famous wait-for-crisis management aka the reverse side of the laid back culture); encouragement of keeping in line and professional mediocrity; (lack of) quality healthcare; dirt; systemic corruption and mafia; massive drinking in connection with ubiquitous handguns; relationships aka love the farang cash machine; farangs always 2nd class citizens no matter what (land ownership &c) -- BUSINESS OWNER'S HELL!
Now that's just to juxtapose two extremes, neither is "the truth".
When it comes to running a business, beware of that viewpoint #2. Freelancers who just hang out with other freelancers on the beach for a few months don't need to care, of course :) For serious business, Malaysia is much more organized and welcoming.
Hopefully I don't get downvoted for this paradise-shattering post -- I still have many Thai friends and I love the country despite all its problems.
I've spoken with a few of westerner businessmen in Thailand now, and they re-iterate much the same sentiments.
My view has become "go there as a tourist who happens to spend several months on business" as opposed to "go there with a view to doing business with the locals".
Likewise I have met some lovely Thai people. They are very caring and welcoming.
You're absolutely right on most of those points. With regards to the racism: I did experience it when I entered night clubs, and it felt weird I had to pay an entrance fee and the Thais did not. But on the other hand, I know foreigners (esp. Westerners, like me) simply cause a lot of trouble in night clubs and obviously hitting on their women. In a weird way, you pay that off with an entrance fee.
In my limited experience, much of the racism I saw Westerners deal with, was most of the times them behaving in a stereotypical Western way (loud, obscene and rude). I don't have a problem with that, but Thai do.
I've come very far by just being over-polite and friendly to everyone I met. Bowing a lot, smiling and always staying calm in conflict situations (e.g. outside at 4am with drunk people).
With regards to dating, I mostly dated hi-so girls, which in the end paid more for my drinks, than I did for theirs ;)
You can renew easily -- or at least could, a few years ago. I lived in Thailand for two years, entirely on tourist visas.
Let me just add there's a marked difference between how OP describes his Thailand experience, and living outside of start-up/expat communities.