I'd say that there should be no issues given six air arrivals over sixteen months. This assumes the previous four arrivals were of similar short duration. I think land entries are hard-capped at two per 12 months.
There is some speculation that Immigration systems have been automated to track both total entries and total duration, with new thresholds for both entries and duration highlighted if they are exceeded. Once you reach the thresholds you might be allowed one more entry or rejected on the spot.
The obvious solution is to get a real tourist visa in one's home country, which can involve multiple entries, can be extended in country and can be re-used with a re-entry permit;
As long as you don't stay >30 days on each visit.
A tourist visa exemption (stamp in for 30 days) can be extended one time in country for 1,900 baht, for another 30 days.
I'd carry any future air itineraries just to show your exit(s). I'd carry any hotel details. Very few people seem to get rejected on the cash requirement - excepting the VoA people, but some do. I personally do not carry the cash, nor do I know of anyone first-hand who has been rejected, but there are reports daily on forums and FB.
I entered and exited Thailand multiple times in a week as a US citizen.
Thai Immigration is said to be clamping down on those who appear to be visiting Thailand for work purposes, even if only for a day or two. A neighbor (U.S. citizen) works for a fairly large entity here, legally and has a Visa and WP, with ~ 80 or so foreigners employed here. They received their semi-annual briefing from Immigration a few weeks ago, and were advised about the requirements for others coming into the country, and for the requirement for reporting the TM30. No clue what your situation might be, but things are changing.