The Royal Gazette announcement states they can ask for proof of the financials again for extensions but makes no mention of this for re-entries. Re-entries it just says they are unlimited for the life of the visa 180 days a time but not beyond the end date of the visa (so it is 5 years, not 5.5 or 6).
This is also what the MFA deputy director general said in Chris's RW4U interview: immigration may ask for proof of the same documentation used to get the visa for in country extensions but for re-entries all that is needed is the passport and visa. He was quite clear on that point, that they won't be asking for proof of anything for re-entries.
there's no exemption from 90 day reporting, so you'd have to do it. Generally though it doesn't matter if you do or don't, unless you need something from immigration in country, that's when it comes up. It's not checked at the airports/borders. So if you never plan to extend but just come and go might not be so critical. Personally I'd do it though.
you cannot stay longer than 360 days continually on the DTV. It's one extension only per entry. You can come straight back but you do need to leave at least once every 360 days.
I don't think this is true. The wording in the gazette announcement specifically said the permission to stay granted would not extend beyond the end of the visa. They changed other visas to work this way too, used be you could get 6 years out of the 5 year Elite this way but now they will only stamp up to the end date of the visa in your last year.
Elite used say more than one overstay in the last three years was the criteria. He'd be under that. And they may well be loosening up now, both Elite and immigration side.
I'm saying if you are applying for a Thai DTV from some other consulates, not the Netherlands, they don't require as many documents. Stuff like the chamber of commerce registration and the signed letter stating you can work remotely. Some other consulates don't require that, just proof of the 500k and a contract.