It is kind of a hassle to actually need to get out of a country and go to it's embassy in another country tp get a stamp or a piece of paper and so on. If we were to be in country, immigration should at least give us a letter whereby we just need to leave the country, come back and hand that letter at immigration and they just stamp our passports and it is done. It is just hassle.

I personally do not see any issues with your current mode. Because you may be staying in Thailand for a certain period but you fly our regularly and within your visa limit.

The only sticky thing I may foresee if it gets too long, like maybe over 180 days or maybe even a year, then it starts to be pretty obvious that you are trying to live there without a valid visa and that could become troublesome.

Just my thought though. Maybe you could do a DTV which allows you up to 5 years and 160 days per entry. Then maybe it will be "safer" for you.

For me, I would pay the money and extend the visa because you could get an overstay stamp and other hassles later if you overstay. Also, if the airline postpones the flight to an even later date, you would be getting into further issues.