I think it's a good and difficult idea. I've started doing that on a few aircraft, but it's a tough job: stenciling varies with users and even time (the French F-8s had at least 3 paint schemes, each with a different stenciling). And for old aircraft, the problem is also that of sources: museum restoration may not be accurate, while old pictures often don't have close-ups (and generally don't have the resolution available nowadays). Most old walkarounds were made by the manufacturer while the aircraft was yet unpainted. In addition, there is often more stenciling on aircraft than we actually realize!
Then you also have a question of format and representation. Should one use existing plans and draw the stencil on those? use parts of pictures?
Surely it can be done, and probably using the Downloads section would be best. Maybe we can trade ideas and decide of how it should be done.
I would favour the following system (keep in mind that this example is quick'n'dirty):
Where one would use pictures (when available) linked to a line drawing. It's easier than re-drawing the whole stenciling. Of course, if no picture is available, drawing can be used. The plan can be set in the center of the page with thumbnails located around it, pointing where appropriate.
I'd also suggest that the aircraft be "broken up" in several sections (in the example I've shown, it could be front, middle and tail sections instead of the complete side view). Doing this would allow smaller images: the hobbydecals stencil sheets are good but the files are very big and yet the scale is not large enough for people to see clearly, as has been discussed recently.
Sources should of course be mentioned pics and line drawing), and (if in PDF format) I'd also suggest that links to existing walkarounds and websites concerning the airplane be listed.
Looking forward to other people's views on the matter.