Sorry, I had to put my cudos in for hot sausage. Cotton candy would have come in 2nd though!
It will probably take you about a full day and a half to fill that pool. It's really going to depend on how much water pressure you have. I know I shouldn't, but we pretty much completely drain ours every year (hubby brings home some type of pump from work). We do NOT drain it till we're ready to set it right back up. I think you'd have major liner damage if you left your pool sit empty over winter. That just lets me really scrub it and we start with fresh water each year. We swim in it while it's filling though, well we wade in it anyway. You will need to get your water tested though. If I were you, I'd grab some of your tap water and run it to have it tested sometime tomorrow. That way you'll have all those initial chemicals at your house already to start putting them in right away.