I am by NO MEANS an expert, but I don't think a mid drive would require more skill. Maybe less because they are more bike-like in weight and handling. As an example, the Specialized Turbo Como is hugely comfortable (for me anyhow; 6'2", 210 lbs, 69 years old), very easy to ride, weighs about 20lbs less than the Yukon, and seems to have the kind of torque more knowledgeable people talk about in a mid drive even though it only has 3 or 4 power assist settings. I test rode one just a couple times and did not have a hub drive to compare it to nor had I ever owned an eBike at that point, so my opinion as to torque comparisons could be way off.
If I had it to do over again would I buy a mid-drive or a hub drive?? Not sure. I'd have to test ride the mid drive again. The Yukon gets me up all but the steepest hills fairly easily without a huge amount of effort. Actually have not walked it up a hill yet except for the time I ran out of juice near my home but have had to work pretty doggone hard standing on the pedals a couple times. It is also good off road on grasslands with those fat tires. The turbo como I test road up grassy hills did great, too. A couple times I certainly would have benefitted from a mid drive's torque, but a couple trade offs would be the higher $ and no throttle (although I rarely use the throttle on the Yukon). The more I think about it, the more I think you might be right about a mid drive requiring more knowledge about gearing. The hub drive's throttle makes it easy to get started even if you stopped in a higher gear. Then again, there is not much of a learning curve in these things. Figuring out gearing is pretty straight forward.
Hmmmm....I might be talking myself into another Turbo Como 2.0 test drive.? In any event, I am glad I bought an eBike. Big fun.