Lotsa stuff there Skill,
My only comment would be that if you really mean "air compressor" you're patience will be severly tested. You need to move a large volume of air (and thereby water), not necessarily requiring high pressure. Most here would suggest a ShopVac, or similar.
My setup's pretty simple so it may not comapre, but I'll put my procedure out there and maybe there's something useful. I have a DE filter on a 22K gal. inground vinyl. So at the pump I only have three lines; two suction for a skimmer and MD and one return for three inlets. Also, I live in an area where frost line is typically indicated at 54" underground for building purposes. While I'm pretty sure only a part of my main drain's below that, through two winters I haven't had a problem.
After taking care of the chems and circulating for the winter, I lower water below the skimmer.
Pull the pump/filter for cleaning and storage.
Start blowing out the three lines with the Vac:
-attach it to the returns and replace each eyeball with a screw-on cap.
-attach it to the skimmer line, attach gizmo after the geyser ends. (if you can find a favorite someone to 'keep their eye on it' before you blow, there's a piece of pie for you in the kitchen!)
[ahem]
-attach it to the MD. This requires a quick hand. When bubbles emerge at the deep end, I quickly plug it with a rubber stopper. No antifreeze for me, thank you.
The other lines are also stoppered and then duct taped to secure the plugs.
HTH.
C.
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