Anytime 2021 would be OK for me
1 - I'm happy with 11 or 14 days in Morocco and would probably get the ferry to Bilbao/Santander and drive across Spain.
2 - Long drives are fine but I'd suggest somewhere between 3-5 hours driving per day is comfortable.
3 - I agree with Roger - it will be more of an adventure without an escort van.
4 - As I said in a previous thread the ideal long journey spares policy is to travel with Roger

5 - Also don't mind.