If it was just wear, I would let it go. The small divots coming out would be my concern. The shoe material is starting to come about, not just worn away.
I am far from an expert, but looking at pictures of the shoes, for the last few years, I have noticed two different type of shoe wear, first is they are wearing, inner more than the outer. The other is where the shoe is coming a part in chunks.
Lots of guys cut open thier oil filter, ever oil change and look for chunks.
I bet they would be good to go for awhile, but if it was my engine, I would at least replace the shoes.
I went with the new hydraulic setup, but I was changing cams and doing a bigbore kit at the same time.
Now that you have had your exhaust off, make sure you recheck your flange nuts, after the first few hours of reinstall.

 

You hit the nail on the head. I could not have said it better myself.

 

Chunking on these is normal. In all honesty these are not bad at all. It iSync belief that heat causes this.
In all honesty the hybrid kit is not the answer for this especially if you can get 60k out of the stock set up. But that is a different subject.
Op did the right thing.

 

One thing we can all agree on is that the Op did the correct thing re: the inspection and that he passed on some useful gen.

 

The sky is NOT falling. You checked them and they look great. Button it up and ride!

I changed mine out at 42,000 (2006 FLHXI) when it was in for big bore and cams, and even at 42K they looked about like yours. Had a lot of miles left in them.

 

OP: It's your bike and you buttoned it up short of replacing those tensioners. So be it.
At the very least I would have replaced them. It's just cheap insurance and the least expensive alternative (next to simply ignoring the whole thing).
Those shoes show wear and they very definitely should be replaced. The only thing 'normal' regarding chunking is that it 'normally' means it's time to replace the shoes.
Remember, peace of mind is worth it's weight in gold. Being stuck somewhere a long way from home just makes that peace of mind bell ring even louder.

 

The front one looks pretty good, the back one I would replace and 'while I'm in there' the front one would be replaced also. How easy do those pop out? I've been hearing members talking about chain slap noise coming from there, is there a way to minimize that?

 

Harley's only last 50K?!

 

No, that is the lifetime of most Harley's, not the life expectancy.
Mine has one fifty thousand miles. These easily do one hundred k most will never see this.

 

For peace of mind he should pick option 4 and change the oil every 1000k.
Park it in the living room never drive it;-)