officially yes, but officially you have to wear a helmet on a motorbike. So if your a tax resident you are supposed to apply for a TIN at local tax office after your first remitence after you have reached 180 days, and then file a tax return by the following March 29th. This has always been the case and hasnt changed. However 99% of expats never bother, and from what i have read, most tax offices have histoically said don't bother as the DTA's and old loophole usually meant there was no Thai tax to pay, and its just extra work for them with no gain. I can't see this changing, but if you do do a tax return and detail your remitance, you have to include a copy of your uk tax return or P60 i believe to prove tax paid.
Thailand has never been a Tax Free country for expats as such, the vast majority don't pay tax in Thailand as they probably pay tax in their original country and there is a DTA in place to cover that. Its not a new tax law for expats, although they make up a large percentage of those bringing income from overseas. The change is to the tax return allowing persons to exclude income if it wasn't earned in the tax year it was remitted. Your 3 scenarios seem to be correct from my understanding, although if you have payed UK tax on that income (usually done at source) there is no tax to pay in the first scenario under the DTA at the end of the year. There are several exemptions allowed on top of the initial tax free allowance that can also be used for any untaxed uk income being remitted. So, yes in worse case scenario you remiited 400k (untaxed in uk) into Thailand without any other exemptions being considered you would be liable to tax on the 250k at incrementing tax rates starting at 5%. The tax due would probably be less than the expense of trying to stay in any individual country less than 180 days.
sorry, misunderstood, it came across that you'd only ever done one TM30, which if you arrived in 2009 is when the first one should have been done. But regardless, the TM30 system has been replaced/upgraded, and the expectation is all effected residencies that have foreign residents/owners register on the new system to gaurentee data exists in the new system, your one of the many examples where the transfer didn't happen correctly. (Cant say for certain they transfered any data). But its pretty simple to register online, make up a name for your residence, fill in the address, upload a copy of the housebook. Then add your details against arrival date of today, leave departure blank, confirm its ok and print off the pdf. Then photocopy the pdf for future use when needed.
the new system is linked to tm30 info and the key that joins them is passport number. So yes you have to have both using the same number. Technically should have done a new one back when you updated your passport years ago. In the old system there was no link and the tm30 was rarely checked. So yes a new one is required, you can register on line if you have the housebook, otherwise you can get the owner to register, complete the form and print off the pdf to keep.
Why would they even consider it? The income from tourist visa purchase and extensions must be more than adequate to employ and pay the staff that deal with them. Without the income the staff would be redundant. Countries that have better terms, give better terms to Thai citizens, can't see that happening with the 3 you mentioned.
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.