Can I obtain a Tourist Visa multiple times while staying in Thailand?

Possible 275 days total 😊 don't worry

I'm in a habit of doing things the right way, that way there is no hassle, but hey that's just me

You can stay in Thailand 6 months in one year with a tourist visa,

I think maximum is 3 months at a time within a six month period

You could also meet the requirements as posted on the thai consulate website in Kuala Lumpur and go get a 6 month METV <- multi-entry tourist visa.

It does have a significant financial requirement and you must show proof of several trips in and out of thailand, but you could wring about 9 months in country out of that visa.

FWIW: here's what those red stamps look like

If you hit the same consulate over and over (back-2-back) you will invariably get the "dreaded red stamp" (which is sometimes not even red :O) It says you used the consulate for several tourist visas and may be denied one in the future. When that happens you can't go to that consulate (or another thai consulate in that country If they have more than one).

At some point you're also going to be called on the carpet by the immigration officers at passport control when they ask you why you're living here on back-2-back tourist visas rather than getting a proper visa.

It's a crap shoot and I know people who have done it for years without issue and I know people who had problems after just a couple tourist visas