Will I face issues leaving Thailand if my visa extension expires on February 7 and my flight is on February 8 at 2 AM?

No

If you already maxed out your 60 + 30 + 7 then your easiest solution is as described, check in online be at the airport early, first to bag drop, go through immigration before midnight. If flight is delayed and bag drop doesn't happen, go straight to immigration desk landside and explain the situation. If you didn't max out, you can still get an extension. Even if you did, you also have the option to go to an immigration office in town before the 7th, and show them your exit ticket and ask for a discretionary 1 day extension to avoid an overstay. If they give it they will charge you 1900 baht. A fine of 500 is cheaper. But it is recorded as an overstay which will count against you for future visits.

I had one day over stay this year I pulled an officer aside and told her she called an other over he laughed and waved me on no problem

Yep, get to the airport say 10pm and check in go to your gate by 1100-1130

Yes - thats 1 day over will result in a fine and mark on your record for over staying

I got to say it “poor planning on your part does not constitute a need for crisis management on our part”

I did this a few years back. Just make sure you get to the airport early as you need to be at the front of the queue so you can get through passport control before midnight.

Big problem if you are stopped before immigration as you have overstayed.fine and you could end up with missing your flight and your passport endorsed

Nope

Technically it seems alright to check in before midnight...BUT what if the flight is delayed or re scheduled....why does one plan this kind of timing and putting yourself in risk

Absolutely no problem, that happens to virtually thousands of tourists every year. No big deal.

Just go through immigration before midnight and even if it's just after midnight, your 500THB fine will be waved. (That only applies on air travel, not on land borders)

As the others have said, get through before midnight, once you are airside I believe you have technically left as you can’t come back through without an escort. So I think you would be good to go.

Never ever overstay!!!

Go to immigration ,they will sort it .

You risk being arrested and immigration prison .

And a overstay stamp.is not a good thing in your passport

Many will blast me ,but it can and does happen

You won't like it much !

Ya ya ya many do it with no problem

Do you want that gamble?

No, just go through Immigration before midnight.

The worst that can happen is you'll be fined 500thb for overstaying 1 day.

Just get through immigration before midnight on the 7th and don’t use the auto gates to leave….get your passport you’re stamped out by an immigration officer.