Harleys haven't leaked since the early 80s (AMF days), unless something is wrong. Mine is a 1999 with 42,000 miles and doesn't leak a drop of anything.
The Evo's certainly leaked. The rear rocker box gaskets on mine would start leaking every two years, which meant taking most of the day to replace. The rear cylinder base gaskets would leak about every three to four years. That meant removing the rocker boxes, cylinder heads, and cylinders. I put an aftermarket device in there that joined the oil passage in the cylinder to the passage in the block, but I still had a leak one year.
I don't like taking my bike to any shop. Every single shop, factory or independent, has scratched the bike at least a little.
I took my bike to one independent in northern Idaho because there wasn't a dealership for a couple hundred miles. It needed a mainshaft seal on the transmission because of a factory defect which was subject to a silent recall (although Harley wouldn't honor it because I wasn't the original buyer). I realized in the first hour or two that I'd made a mistake taking the bike there, when I saw one of the mechanics swearing and struggling to hold a rear wheel up in the air and insert the axle, spacers, and other parts to put the wheel back on. Back home I had a chain lift, and just lowered the bike over the wheel until it was at the right height to insert the axle and parts.
They got all the parts back on, but the mechanic forgot that the mainshaft had a key on it, or maybe he never knew that to begin with. He didn't line it up, but just torqued down the nut on the clutch, and destroyed the clutch basket. It was two days for UPS to get a part. After I'd been sitting there five days they were ready to button it up. I asked them to put red Loctite on the huge nut on the crankshaft, and on the clutch nut. Both are left-hand thread, and can loosen from centrifugal force, which is why the factory manual calls for red Loctite. They were purists, though, and didn't believe in Loctite. I told them to put it on anyway.
When I got home, I had to redo what they had done, because they put in the wrong mainshaft bearing (sealed instead of open cage), and the wrong seal, which was leaking by the time I got home. I found that they hadn't put on any Loctite, either.
Once, after re-jetting the carb and setting the timing, I took the bike to an independent shop to have them double-check the timing. On Harley's there's a bolt at the base of the cylinders that you remove to see the timing mark on the flywheel. There's a clear plastic bolt you put in to keep the oil from spraying out while still being able to see the mark. The timing is adjusted by turning a timing plate.
The mechanic didn't have the plastic plug, and so when he started revving the engine, there was a cloud of oil in the air, settling on the bike I'd just washed and waxed. He was revving the engine up to 3,000 to 4,000 rpm. I told him the manual says to time it at 1350 rpm. He said it didn't make a difference. With the old style points and centrifugal timing weights, it doesn't make a difference, but with electronic ignition it does. I kept arguing with him, and he kept insisting he was right. Then he said he couldn't retard the timing enough without filing the slot in the timing plate to turn it even further. Not surprising, considering he was trying to time it with the spark advance so far off. I told him to put the plug back in the block and give me my bike back.
I've had nothing but bad experiences with dealership and independent mechanics.
