My specific interest in the OP's point is that one of my types would be very
difficult to transfer as there is no longer a sim for the aircraft and, as far
as I am aware, no TRE that is EASA approved. Thus it would be possible to use
the 500 hour route but the check-ride would be an issue when it came round.
Consequently, under the new regs requiring both non-EASA and EASA lic for
European OPERATORS in Europe, I might have a problem after the derogation -
although the OP's information suggests all would be well as long as I was flying
the type on the register of the third-party country for which I had the licence
and rating and was in possession of the equivalent EASA licence.
DefDefect,
My understanding is that article 8.5 exactly address your situation, as you have written. Of course, you'll want to check from a more authoritative source than an anonymous bloke on pprune. To be honest, it's pretty plainly written.
Having said that, the plainness of the text does seem to work against the M register case. It suggests you'd need a TR issued by the Manx authority. This is potentially a huge issue for the M, so putting it bluntly, I'd expect their customers to push them to do some work on this!
There is a further problem with Types that do not have a type rating on a 3rd country register (eg. the King Air on the N or M) but require an EASA Type Rating (or type-specific Class Rating). It's not clear whether the qualifications acceptable to the 3rd country would satisfy 8.5 or whether an EASA type qualification would be needed.