Yes, some details missing...
Objectives: mapmaking for undergraduates (but not cartographers), experimenting-fun via pursuit of personal connection to map shapes (we are an art college)
Image shown is titled 'Sun Island'; designer looks to have started with a high contrast image of Elvis, turning that into island shapes atop water background; it's a conceptual approach, thus complicated
Since an Elvis map has already been done, second-level challenge would be to have students 1) find a framed orthogonal view of a land-water-scape that matches his/her own portrait (instead of Elvis), and 2) lay that atop (say) a Google Earth Pro section it best matches, 3) add some creative-copywriting-labeling, and 4) create a GEPro fly-though from one student's layered image to another
I teach at an art/design college whose students are quite good at Adobe Creative Suite and Premiere (I can teach them how to export a fly-through movie from GEPro, import into Premiere, add sound, and titling, etc.), so that's half-fun/half-tech to them, easily do-able. The software vector-matching solution requested is trickier.
Yes indeed, I worry about your caveat. But then look at Indonesia, or the west coast of British Columbia (e.g. Salish Sea area), et al., and what might happen if/when one's search routine for vectors 'zooms in' at larger scales. BTW, I don't mind being told it's almost impossible, that's the honesty that makes forums useful.