The reason I am going for the Rolleiflex is because I want a street/travel camera that is more compact, more light and more quiet than the Hasselblad.
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Fast focus, TTL metering, well coated lens are all important to me and the ones I would lose with a new model are not.
Ari, I'm not sure how important is TTL metering. My uneducated guess is that TTL would be used most in studio - and in those cases you can use a separate light/flash meter.
If it will be used primarily for street shooting with fill-in flash, you have a valid point (regarding TTL metering).
But, given that you said you want to be unobtrusive, I don't really see how you can be "invisible/unobrustive" with
any kind of flash. So, for myself, TTL would be of minor importance in such a situation (street shooting).
Once you strike the TTL metering off your list of features, you might as well use a second hand (used) Rolleiflex, which will be much cheaper than the prices you quoted.
If you can find a used one in Greece, I would recommend trying it before buying - or at least comparing a good used one to a new one - and seeing whether 5-10x difference in price is worth it (for the intended purpose)....
I can only offer my persepective - I purchased a used Rolleiflex T in Austria a couple of years ago, for about 280 EUR (in almost pristine condition, the lens was a bit cloudy because of the evaporting grease). After about EUR 50 for the cost of cleaning the lens, the camera was as new!
It does have 75/3.5 Tessar lens, though. The 80/2.8 Planar (or Xenotar) would probably be more expensive - but a good used one should not cost much more than about 500 EUR. Compared to about 3500 EUR for a new one, it IS quite a difference in price!
OTOH, any kind of Rollie (even the new one!) will probably have much dimmer ground glass than your Hassie (particularly if the Hassie is equipped with AccuMatte prism/finder!).
So, my suggestion is to try before you buy - whether new or used...
Denis