Kinga Tanajewska did the Vladivostok run earlier this year and seemed to find it OK, but then she does seem to be pretty good at networking and finding places to stay/people to help. Personally I'd prefer to do it with a buddy but you certainly can do it solo if necessary.
Russia | On Her Bike
You should be OK for weather in August, though the summer is coming to an end by then so be prepared for hard conditions on the higher roads. If you plan your daily mileages you could probably avoid the need for most of the rough camping and scabby little towns and aim for cities with real hotels.
Regarding Ukraine insurance you should be able to buy it at the border.
9 most useful Ukraine driving tips - Active Ukraine
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