Nice idea, and I would say quite managable. Just bear in mind once you hit Ukraine the on road will be like off road a lot of the time, especially in the mountain areas!
I like the Ukrainian Carpathians because it has a real fronteir feeling to it. But there really are very few through roads in parts of it,even though it is not very rugged compared to say Romania.
Google maps is your friend there, paper map options are limited and unreliable even for hiking. As you'll be relying on logging tracks you should be able to make them out.
Kosiv, Rahkiv are worth a visit , one for its market and the other because it will make you think you are at the end of the world, almost Mad Max style. Osmoloda is worth passing through, its a dead end logging town, you come in from the North and I would love to find a way out heading South!
I'll hopefully be heading the same direction but on 4 wheels next year.
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