@Andrew Girgis @Allen S.really nailed it with that comment.

It is likely a popped nail.

You nail those fundamental's, the market won't matter, you will always sell fast and for top of market.

You bring a narrow pry bar/putty knife up there, loosen the shingle tabs from the tack strip on the shingle above it, pull the nails out of the bad shingle and nail a new one in.

For the most part I give it a lot of the raw info (vs asking it to come up with all the points) and ask it to polish the text in a professional manner from the perspective of a real estate agent.

If you use 10 penny nails, thumbtacks, staples, etc, it's coming out of your deposit.

I probably would let the small nail holes slide.  

Now granted, the color may be harder to cover and may take more time and cost, but the judge wont let you charge the whole cost to the tenant...a portion at best.Same with holes in the walls....if we are talking nails, tacks, etc and the tenant has been there a few years, that's considered reasonable....to expect nothing is not reasonable........ if the tenant attempted to FIX the issue without your approval and made it worse, then you can ding them for the extra work.There is a big difference on what you emotionally THINK/FEEL you should be able to hold the tenant liable for and what will actually hold up if they take you to court.My eviction lawyer often tells his clients to go ahead and try and charge for that stuff.......many tenants wont put up a big enough fight to take it to court....but if they do, you will lose so be prepared to pay it out

This is a very tough piece to nail down.But once you line all three of these pieces up, now you have an investing network set-up. 

These were gaping holes, not just nail holes.