Travelling with both passports is acceptable, i used to connect the two with an elastic band on the relevant current permit page and never had issues. The deadline for getting the permits moved over will be your next 90 day report, as you'll have to update your tm30 to reflect new passport no. Then within 14 days of 90 day report date visit imigration get the stamps moved and do your report in person in one visit. Saves you a trip.
it maybe fine and you'll be able to do it online, but within the system your succesive 90 day reports are linked, and there will be an anomoly in that there is a difference in passport mumbers which is part of the database key, so technically a first report which could cause a rejection. Do this one on site and the following ones on-line.
I would suggest filing a new tm30 using your new passport tomorrow, delay getting the stamps moved until the 2nd, and once there in your new passport go and personally do the 90 day report while you are there and within the 14 day window.
unless you intend to leave the country and return within the under consideration period, as your current re-entry permit is no longer valid in that period, and you end up paying twice to cover the existing extension.
Watch the video at home first (from DLT site not utube) and take a print out of QR code with you as proof you've watched it fully, as part of your documentation.
Dont wait for the approval to start transfering 40k, as you may not have 12 months of payments recorded at the point you apply for 2nd year extension, (you may only have 11).
agree, the drop dead date for getting the stamps transfered at immigration is prior to the next 90 day reporting, and the TM30 after arival should reflect the new number.
The 3yr non-b doesn't support work permits for employment in Thailand. It is basically to allow foreign nationals to fly in do some meetings, give some training, sign some deals etc, multiple times in a 3 yr period.