Need help re-plumbing!

Craig,
Thanks for the info. I now get what a cleaner line is! I agree, sounds like a good idea. I currently have 3 semi automated pool cleaners, they are 10, 12 and 19 years old! Hopefully, they will get better at it with age! I will look into the zodiac cleaner, due to the "Semi-ness" of my existing cleaners (kids)!

I was hoping to miss the old lines, but seems I managed to hit almost all of them! As I was planning on replacing them anyway wasn't a big deal. The biggest downer was hitting my pool light run on the far side of the pool. Not really a big deal as electric is what I do for a living but unraveling 100+' of THHN #14 from the trencher was a drag! I knew where all my other lines were (gas, main electric and phone).
 
Hah, I like that. My semi-automatic cleaner would be me (kids are 8 and 5 and not quite ready for prime-time). The nice thing about an automatic cleaner is that the pool stays clean all the time, not just right after I vacuum the pool out. We used to have a flaky pool guy who serviced the pool. It would look nice right after he cleaned it, but within a few days, would have a bunch of leaves at the bottom (due to lots of nearby trees). The biggest factor in getting rid of him was that the automatic cleaner could keep the pool clean all of the time. It took a bit of futzing to get it working right, but now the pool requires much less work and nearly always looks great.
 
Here are some updated pics. Have made some progress. I now have the trenches cut into the deck and dug out. The local pool guy was by and recommended replacing the skimmers while I was at it. The pool was built in 1996. I do not know if they leak or not. A quick visual inspection and they look fine. No apparent leaks now that I can see the outside of them. Any thoughts? After 16 years, and since I am this far, should I just do it?

Again, Thanks for all the help!
 

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I would check to see if the lids are fitting correctly and then check the flappers and see if the sides are rubbing. This would tell you if any ground shift is putting pressure on them. Looks like your going to be doing some flat work anyway cheap insurance would be to replace them.
 
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