I've been a bit apprehensive to ask this, because I'm fearing that something here is going to cost a lot of money 
I have a few spots around the pool that really need some attention. I'm not sure of the proper products to fix these deficiencies, so I'm hoping someone here knows a lot better than I do. Here are the pictures.
1. Expansion joint is ripping. This was "fixed" poorly by the previous owner by slathering it in silicone RTV. Obviously that did not hold. Is there something I can use to restore the flexible joint material?

2. The grout about the tile line where it meets the coping(?) is cracking in multiple places all around the pool. I'm worried this will allow water to get behind the pool shell and erode the fill.

3. Similar grout damage in one of the skimmers. Same fear here, I don't water getting behind that and causing problems. Obviously water gets splashed into the skimmer all the time when the pool is in use, and I'd like to prevent this from getting worse.

4. The spa has a few places where the grout between the bricks is failing. This section is normally hit with water when the spillover is on. I think that some of this brick got damaged when water seeped behind the brick and froze. There are a few spots on the spa like this.

Is there any DIY solution for these problems? I know absolutely nothing about masonry, so I'm not even sure where to start here. Any direction would be much appreciated!
I have a few spots around the pool that really need some attention. I'm not sure of the proper products to fix these deficiencies, so I'm hoping someone here knows a lot better than I do. Here are the pictures.
1. Expansion joint is ripping. This was "fixed" poorly by the previous owner by slathering it in silicone RTV. Obviously that did not hold. Is there something I can use to restore the flexible joint material?

2. The grout about the tile line where it meets the coping(?) is cracking in multiple places all around the pool. I'm worried this will allow water to get behind the pool shell and erode the fill.

3. Similar grout damage in one of the skimmers. Same fear here, I don't water getting behind that and causing problems. Obviously water gets splashed into the skimmer all the time when the pool is in use, and I'd like to prevent this from getting worse.

4. The spa has a few places where the grout between the bricks is failing. This section is normally hit with water when the spillover is on. I think that some of this brick got damaged when water seeped behind the brick and froze. There are a few spots on the spa like this.

Is there any DIY solution for these problems? I know absolutely nothing about masonry, so I'm not even sure where to start here. Any direction would be much appreciated!