It has been six or seven years since I've been to LOS, and I haven't been paying close attention, but I think many rules have changed. So I would ask to be directed to any appropriate links here on Thai Visa.
I am a retired Canadian living in Malaysia (MM2H) and would like to do some short trips to BKK/Hua Hin. Is it still the case that I would only be able to do two such trips (of less than 30 days each) if I arrived by land at a border crossing?
Is it still advisable to have minimum 20,000 baht in cash to show at border?
If I do two land border crossings, and then wish to do another short trip within the same calendar year would I be able to do this if I arrived by plane?
I have read about the health insurance requirement. Is this applicable to me in the scenarios described above (visa exempt)? or is it only for other long-term visas?
Any other advice that might apply would be appreciated

There is still a limit of 2 visa exempt entries per calendar year at land border crossings. There is no limit by air.

Insurance is not required.

Thanks for the reply.

For short visits (say, less than a week) you ought to be able to make quite a few by air each year before you would run into a problem. Have the 20,000 baht equivalent in cash, just in case. Entering by land at the border from Malaysia, in particular, you might be asked to show it.