Remote federal employee? I suggest you double check with your manager about working remote from overseas, especially if you are talking about the American government.
I’ve flown in and out of Singapore maybe 6-7 times (I’m a Pass holder) after I got my DTV with no issues on either side. Just make sure you submit your arrival card online so you can use the e-gates with no issues.
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You will get a receipt for your arrival card via email that you can show if anyone asks for whatever reason.
In the last few weeks I’ve noticed a delay in Wise to Bangkok Bank transfers also, generally for larger amounts though. I transferred 100k yesterday and it took about 12 hours. Transferred 650k a few weeks ago and it took about a week to clear.
Just wait it out. Personally, if I was in tax resident status and not actually earning money here I wouldn’t get a TIN or file anything until I was forced to. These changes are for catching high net worth individuals who are evading taxes, not your average expat.