I think you had it right the first time, that is a "stealer" you dealt with. I'd not darken his door again.
Engines don't sweat, people do. But engines do leak when they're built by H-D. Not terribly uncommon for the rocker cover gaskets to develop seepage, and before handing those crooks any money you might want to just try snugging up the rocker cover bolts and cleaning off any oil residue, then ride for awhile and inspect again for leaks. If you identify a real oil leak and can't fix it yourself, find an independent shop to make the repair. Replacing a rocker cover gasket doesn't cost anywhere near $800.
If you have a dark stain directly around the spark plug, that can be just heat discoloration, or possibly the result of combustion gases getting past the sealing ring of the sparkplug. It's very obvious on the silver engines, not so much on the black ones. I had that occur on my SEEG shortly after I bought it; I cleaned the surface as best I could and made sure the plugs were installed correctly ever since (15 ft lb with a torque wrench), and the stain didn't get any worse over the next 5 years.
BTW, I don't exactly understand the deal about giving them $150 just to look at the bike and give you that BS response without any attempt to fix anything. Is that the way stealers do things in Canada? I thought the ones here in the US were bad, but that makes the places around here look almost reasonable.
Jerry