What should I do about my visa situation in Chiang Rai with an upcoming overstay?

An overstaying stamp raises red flags if you come back to Thailand

Get the extension and keep your record clean.

Overstay is 500 bht a day so 1000bht,best to pay the immigration 1900,only 900 more and avoid any overstay passport stamp as it's a red flag that you did an illegal action 🙏🏽

You should NEVER go on overstay. Even a random interaction with the police like a checkpoint could result in you being jailed, deported and banned from Thailand for 5 years for one day overstay. Plus if you are traveling to Thailand 2 or 3 times per year, they have been giving greater scrutiny to people who come often, and having an overstay of any duration may cause you to receive increased scrutiny in your future trips.

2 days overstay would be a 1000 baht fine, so you're really only paying 900 for the extension, and for peace of mind.