I am currently running my pool open for the winter, this being our first winter and our first pool- we have similar weather to what you described. Right now, I am just using a leaf net- looks like a giant hair net- to catch leaves. Even then, we have trees with small needle-like leaves that get through the net. I run my autovac for a couple hours each week (and remove it when it is done- I have a Ranger also) to get any dirt and junk that has gotten through the leaf net. The leaf net will come off once the leaves are all down. We may put it back on in the spring, as we tend to have lots of plant stuff come down then too.
I have a basic Intermatic freeze-timer on the pool- it is supposed to turn the pump on when the temps get near freezing (of course it froze before we got it, and then we have had record high temps since we installed it). It also runs the pump during our daily pre-set hours as well. The leaf net floats on top of the water and the pump runs just fine. We have to pull the net out of the way when we use the vacuum, as it tangles the hose, but it is not hard to do.
My general goal is to go without draining/winterizing/covering. We would be constantly battling the high winds and crazy weather here. Plus torrential rains drowning the cover. Plus storing the cover for 7 months of the year (summer), plus they only last so long, plus our winter is only Nov-March. So going without the cover seemed worth a try. If we get a real winter (ice, snow, freezes, etc) then we may rethink this and winterize for real. The companies that I have been ordering supplies from (
http://www.amerimerc.com and
http://www.intheswim.com) get them to my doorstep in 1-2 days, so if I do decide to cover, the cover will get here before I even get started.
When I was in the process of deciding, I read every post on here about it that I could find. A couple people had tried leaving the solar cover on all winter and ended up with it partially breaking down in the water/ cloudy water. My solar cover seemed to be assisting an algae problem that I was not able to completely defeat until I took it off. The water being around 60 degrees now means that it stays very clear. I just added Polyquat the other day to stop having to add bleach regularly for the winter. If that fails, then I will go back to bleach. With cool water, I only had to add bleach a couple times a week.
So far, I am good with the decision to leave the pool open for the winter. If we do get a real winter and end up winterizing, I would probably lower the water level just enough to keep it out of the skimmer, but would disconnect the hoses and drain the pump and filter to keep them from freezing. We have a little plastic disk that lets us seal of the eyeball return. I might also consider a skimmer-cover- like a tupperware lid for the skimmer- lets you keep your water level up without water getting into the skimmer and freezing and cracking it- several people do that on this forum.
Hopefully someone else can tell you about running the pump with the winter cover.