Oh, wow, that IS a nightmare....I am a huge chicken when it comes to bad weather--there's nowhere I'd rather be in a storm than home with the blinds closed so I don't have to know what's happening outside!
I don't know anything about main drains, because my IG pool doesn't have one, so hopefully somebody else will come along to give you useful information about that.
I think that the insurance probably will cover the liner under "wind damage", just as it should cover your plumbing. I'm not sure about your insurance company, but mine replaces at current market value..they wouldn't depreciate the value of the liner. In the eyes of the insurance company, it was a working liner, regardless of how old it was.
Your bleach and CYA can be added simultaneously--remember that it's going to take several days for the CYA to dissolve and start to protect your chlorine, so get it in as soon as possible. I would go ahead and add bleach as soon as you have a way to circulate it. You're going to have to add the bleach daily until you have a measurable CYA level, though, so make sure that you have plenty on hand.
As for adding bleach through the skimmer, (assuming the pump is running), the only problem with it might be fading of the liner around the outside of the skimmer plate if you don't pour it slowly enough...otherwise, adding it through the skimmer is fine. Personally I'd rather add it through the returns, though, so that it gets to my pool before it gets to my filter...I don't want to waste any by trying to "sanitize" anything that's stuck in my sand filter.
You're right in that TA and pH are the other values that concern you when restarting the pool--running a test on your fill water ahead of time might tell you how much Borax or acid you need to have on hand for the refill.
Don't know about the pump motor...I'd say that if it were still running when you found it, and if it primes okay after the pool is refilled, you're probably okay...but I don't know much about them so maybe Poconos or somebody that is a motor expert will stop by soon.
By the way, when your skimmer plate sticks, pour a cup full of tap water from the pool or hose over the plate and it will lift right out!
Good luck.....you have a mess on your hands but hopefully your insurance company will come through and get you up and running quickly.
Janet
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