Here is a video showing the cylinder approach. the first thing is to rebuild the cylindrical surface with more control points and degree = 3. The you can start pushing those points around to develop the shape. A critical challenge is getting the background bitmaps properly scaled. I did not take this very far as it can be a time consuming task. Once you get the basic form you slice off the ankle sleeve, Shrink both surfaces and continue refining. https://global.discourse-cdn.com/mcneel/uploads/default/original/3X/2/c/2c3742f33a5acc00d9e478d5bb66ad4b2438d740.mp4
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Wow! I’m very very thankful for you taking the time to actually do that video for me. It will help me a lot to see your approach. I think that type of workflow suits me very well. So again. Thank you!
I will try now and se what I can do. Maybe I will come back with a question or two 
@ rcmcdougle
You said that I should add 2 Isocurves in a post above. Do you mean that I should insert knots and get “knotlines” on either side of the seam or can you add isocurves? I’m not 100% familiar with Rhino (yet).
InsertKnot is the correct approach. You can enable symetrical and control the U or V placement from the command prompt. That does generate additional isocurves. If you always grab those 3 control points (the seam and the new 2 flanking points) for movement, curvature will be maintained fairly well.
From my perspective, this is not a precise way to model but it is a way of getting to forms that could then be developed into something more precise.
Does ski boot manufacturing still make use of a specific kind of last/tool? Such as a detailed mesh which is then converted/parameterised into a UV surface?