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Leaking shower door track - help!

Hi all -

We've has some water damage on the drywall at the corners of the shower door track in our bathroom for the past several years. It is slow-moving, and we've never seen any water - just the damage on the wall. We had a handyperson come out a few years ago to look at it, and they thought the water was getting through at the inside corners of the door, and this water was snaking around the corner and slowly damaging the drywall.

Recently, I pulled up the caulk in the shower to replace it, and found an area of missing grout under the lip on the inside of the shower. I had a grout company come out and replace the grout there, as well as patch a few other cracked areas they found, and re-caulk the entire shower.

Unfortunately, we're still having water escape the shower - I did some testing with a squirt bottle over the weekend trying to find where the water is coming from/coming out of, and it appears that it is getting under the shower door track and coming out the other side. The water sits on the ledge, there, and some of it may run over to the drywall which would explain why the damage has been happening slowly. We had been under the impression that the grout company re-caulked all of the shower, which should have included the outside bottom edge, but the caulk there is still pulling away/allowing water through. We're having the company come back out to re-caulk there to be sure it has been redone.

Here are my questions:

1. By looking at the photos - are there any other routes we should be exploring that we're not thinking about? I'm attaching photos of the water damage on the walls, the missing grout issue that was discovered when I pulled out the caulk, and the water leak that I was able to find on the outside ledge of the shower door after I poured water on the inside ledge. 

Trackquestion.jpg is the photo referenced in questions #2 with the red and green arrows.

Wall.jpg and Wall2.jpg are photos of the water damage on the walls.

MissingGrout.jpg is a photo of the missing grout under the inside lip I found when I pulled the old caulk.

OutsideCaulk.jpg is a photo of the current caulk on the outside bottom of the shower door that is pulling away from the metal

WaterLeak.jpg is a photo of the water leak I discovered after pouring water on the inside ledge and letting it sit

2. When we have the outside of the shower door track re-caulked, should we also have the inside of the shower door track re-caulked? It appears that the water is splashing up on the ledge inside the shower, and then slowly seeping under the track and then escaping the other side. This seam was not caulked originally, but I wonder if it should have been? I know there are weeping holes we should be careful not to cover up, but if we caulked along this seam inside (green arrow), as well at the outside seam (red arrow), would this stop water from getting under the track?

Thanks so much for help you can provide - we're really out of our knowledge element, here!  


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