I actually hate dealing with immigration and have used an agent for the past 3 years... have never stepped into an office since Covid. Some people say its a waste of money and you can do it yourself, but I dont consider the money to be a significant amount considering the time and hassle you save. Time is money.
If you're abusing the system and living in Thailand on tourist visas and visa exemptions, you probably have a very good chance of being asked. If you're a real tourist I'd say the chances are almost zero.
I'm pretty sure you need to cancel the original visa (I think you're on an ED ) if you have plans to stay in thailand long term later on. My buddy was in a similar situation as you, canceled his visa last week at CW and is in Lao now for a month. I'm not sure why you would transfer an expired visa to a new passport though.
Seems you've been in thailand for a good year or so on covid extensions, tourist visas and/or visa exemptions. You probably should look into a more long term visa option or go back to the states for a few months.