Can I get another 30 days in Thailand by flying out and back in or should I do another border run?

Hello Everyone!! I have a rather long situation that I need some advice with. I am a US citizen.

Before getting into it, I will just start with a small primer to avoid confusion. I am on something called a Watson Fellowship (basically a rare/odd scholarship that supports me to travel around the world for a year). The Scholarship is too unique in nature to possibly give me an education Visa. I have checked with the Thai consulate extensively about granting me a special visa and I recently found that it was not possible unfortunately.

Here is my current situation:

I was in Cambodia in October and I did a border run and crossed through a land border into Thailand to extend my Cambodian Visa at the time.

In November I flew From Cambodia into Phuket in Thailand, and was granted the free 30 days on arrival. The next month I got this extended at a Thai immigration center granting me another month. The stamp on this said I had to leave the country by mid January.

In January I had to “leave the Kingdom” at which point I did a Border run to Ranong— I used the boat ferry to very briefly go to a Myanmar port and return back to Thailand, so that I would be granted another 30 days. Another month went by and I got another month extension at an Immigration van. The stamp again said I had to leave the country by March 10th

At this point I have to leave the country by March 10th but want to stay for another two months though (longer if possible). I was considering doing another border run to Ranong-Myanmar but am aware that there is a law saying you cannot enter through Thai land borders more than twice in a “calendar year.”

Now technically I have entered through Thai land borders twice in a year span (once to renew my Cambodian visa and once using the ferry to Myanmar to do a Border run)…However this is not twice in a Calendar year span, as I have only done one Border run in 2019. However I am worried that the Thai officials may use their discretion and not see it quite that way, and there will be a misunderstanding over the “Calendar year” aspects or how many times I am allowed to cross the Thai land border. I do not want to get stuck at the border obviously.

I am now considering flying in and out of the country in a day in order to get a free 30 days again, but have a few questions because I am not super knowledgeable on this part of it.

My three questions are these:

1-If I fly in and out of the Country (Say to Kuala Lumpur, Malaysia and then back to Phuket) will I be granted another 30 days on arrival?

2- If the answer to question one is yes, then once the 30 days upon arrival is up, will I be able to extend for another month at a Thai immigration van or center?

3- If I decide to go the whole border-run route, do you think it is risky to do so? Their policy does say a “calendar” year, and it would be easier/cheaper than flying, but I worry that it could be risky and cause an issue.

Thank you!!!