The patriotic slogans and artwork are the best bit about VVS skins. I never use a font for anything like that, it just does not look right.
Ideally if I have a photo I will try to resize, rotate and deskew the part of that photo containing the text, noseart or markings until it matches the skin. I import the edited photo as a layer in the skin and try to match features like a filler cap or a hinge line on the photo to the same part on the skin, resizing the photo until the scale is exactly right. Then I make a new layer and use a line tool to draw the text by hand, tracing over the photo. Best bet is to use a false colour like red when doing this.
For complex multi coloured noseart I will sometimes make a whole new multi-layer image 2 or 4 times oversize. When done, I make a copy of this, merge the layers, shrink it and import it into the skin.
The worst thing about VVS skins is the lack of good quality information compared to Western or even Japanese aircraft. Photos are less likely to have an accompanying squadron identification as the VVS had no formal squadron marking system like Western air forces. You often find the same few photos cropping up in 3 or 4 different books too.
These photos are often of too poor quality to get a lot of information about camo demarcations etc. Individual Soviet factories often went their own way on camo schemes, unlike say the RAF who strictly controlled the layout. There is a lot of quite heated debate in Soviet warplane forums about the correct colours for VVS planes too, no one seems to really know. As a result profiles are less accurate for VVS skins than for any other air force. You can often find 2 or 3 completely different looking profiles all based on the same photo.