My experience has been during winter that either I'm a slave to my cover or a slave to my pool water, and being surrounded by so many trees (pines, oak, etc.), I find I'd rather maintain a cover.

I use the Rule automatic pool cover pump ($140 and it lasts a number of seasons). If big rains are predicted I just flip a switch and it's ready to go when it senses water. I've a 300-ft. garden hose attached to it that winds down through the lower yard, under the privacy fence then runs along the 2nd driveway, well-hidden by leaves, and ends up at the curb. That way when the pump is evacuating copious amounts of rainwater, it doesn't drain onto my property (or ultimately my neighbor's).

During the very long leaf season I regularly (weekly, sometimes daily if I don't like looking at it) either rake, blow or use my long pool pole with an old pool brush to push/pull debris to the edge and up where I dispose of it. That way the pool cover pump also doesn't get clogged by debris (well, it still does but I just quickly clean the screen to it). Yes, this goes on for virtually 8-9 months, because in the spring there is just loads of junk coming down from budding trees as well. So...there's never standing water on the pool cover and it doesn't get nasty at all. In May it just takes a warm day or two after the last rain to completely dry before a friend and I employ the sailor technique to remove it (folding one large lap onto the next until it's out of the pool and then rolling it up for storage).

Also, I can monitor my CL during the entire time by pulling up a flap I made over the skimmer with some scissors (and a lighter to seal the edges of the cut cover edges of the flap) and if I need to add any CL I just put it in the skimmer and run the pump awhile.

Because I have continuous double-tubed water bags around the entire circumfrence of my 16x32 in ground, unbelievably when I open 9 months later, not only is the water as clear and pretty as it can be, but at most there might be a silver dollar's worth of grit in one corner of the deep end. The alternative to all this would be looking at my pool become very, very dirty -- beyond imagination, really, despite heroic attempts to keep it clean - in fact, it would be impossible in my environment to do so. No worries!