Just book a flight you can cancel. When the visa is rejected, cancel the flight. When the visa is approved, decide if it is better to cancel and book cheaper flight or just use the booked flight.
Leave on day 89 and you do not need 90 day reporting. You can keep doing that forever, but 90 day reporting is simple and free, and takes much less time than a borderrun
I do not see you litterally need to bring in everything. Proving you still comply is not that strange. And documents that are not time dependant you still have, so what is the difficulty? Showing your soft power is still going on, or your still work remote is not that difficult. Show online you still have 500K is also easy.
After deregistering from Netherlands, you cannot apply for DTV from Netherlands I think, so then you should apply from another country. Is there a reason why you want to deregister?
is this a conspiricy theory? Just checking you still comply is making it difficult for no reason? It is only difficult when you do not comply to requirements anymore...
correct, so best when you want the full stay of 180 days, to do the first 90 day report just after 90 days, using the grace period of reporting, then the next will be after your 180 days.