Hi and welcome. A great first post full of the sort of enthusiasm I'm sure I used to have
Your schedule sounds as though you'll be all set up and ready to go in mid winter. Many of the Euro options are pretty miserable at that time of year - cold (not so much of a problem), dark, wet or snow covered and, often, shut. There's plenty of bike related 'mini adventures' available in winter - rallies etc - that certainly fit the 'adversity and struggle' requirement (google Elefantentreffen for the biggest one) but heading south into north Africa would be my suggestion. Check out Chris Scott's Sahara website and see if you get any inspiration there ( https://sahara-overland.com). If you've not been before there's plenty of culture shock, mountains etc in both Morocco and further south.
ps. Don't knock riding the Amalfi coast (in summer anyway). The number of 'fly n drive' tourists trying to do it with a bottle of wine in one hand and a pair of binoculars in the other make it as white knuckle a trip as I've done in some time
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