I did this
route several times both way. As you said, the prevailing winds are northerly / west northerly. Sometimes southerlies comes but this is usually in spring or automn, very rarely in January..
-if you find a southerly, go, go, go.. as much as you can, southerlies don't last long.
-particulary after Kusadası, it will be damn cold, after Dardanelle it may even snow..
-if the northerlies are strong, plan where to hide. The Furino and Chios channels are critical, watch out for the right time to pass, usually late in the night or early in the morning the weather is quiter.
-In the Dardanelle straight you will have 4-5 kts of
current against you and because of heavy traffic + city lights, the night sailing is very difficult. Before crossing the straight, you can spend some time in Bozcaada island marina. (if you go in dark in
winter, there will be nobody to take yr lines..)
-From there on it's easier. In worst case, go behind the Marmara island, Mürefte is an option but the entry is shollow althought I believe you can make it with 36 footer.
Good luck
Yeloya