Do not listen to anyone who haven't done a border run in over 20 years. Old dude love to patronize younger people here with awful info just to make you feel guilty. I'm 37 and have been living in Thailand since I was 25. I'm married now but I'm very familiar with a lot of the border. I live very close to Nong Khai border. Getting denied by land is not a thing in your situation unless you try Poipet which are notorious for bribery. The big 3 to avoid are Poipet, BKK and Phuket airport. The rest of the country is still easy to enter from.
You have received mostly bad info so far (from Kool, John, etc). There is no such thing as getting denied entry by land except in Poipet. You have done 0 border run in 2024 so you can still do 2 by land. Every time someone come up with anecdotal evidence that someone got denied, it's one of three things: 1) Poipet ; 2) It was his 3rd attempt in a calendar year, or 3) A border officer asked for proof of fund or onward ticket and that person didn't have it. It's never due to something else. If you border run Nong Khai or Mukdahan, they do not ask for any proof of fund or onward ticket, so I usually go there. Keep in mind that BKK and Phuket are strict, but these are by air and doesn't apply to what you want.
Everyone know that, but this isn't the topic discussed. The topic is about you wrongly stating that "an overstay stands out in your passport like a fart stain on a wedding dress". This is what I called "factually incorrect", because it is.
There is no such thing as spending the night to increase your odds. I live 45 min from Nong Khai border, you can leave and come back 15 min later no problem.
The 2 visa exempt land entry has been there for 6-7 years approx? OP is talking about recent toughness at the border which is not a thing. And what you are describing with illegal work is unrelated to entering by land, it's a different subject which, yes, it's harder to work illegally unless you do it online.
It's a common myth that border run is getting more difficult in Thailand. What is more difficult is entering from an airport (especially BKK and Phuket), but the borders are really easy to enter from with no issue.