I just responded to your other thread, but forgot to mention what a beautiful pool and yard you have. My entire neighborhood would probably fit on your lawn.
Having a cover is definitely worth it. Mine probably does more to keep my pool warm than my expensive solar array. Based on my brief experience and some reading on here, I don't think expensive thick covers are worth the money. If I were you I'd consider this one:
I personally think a pool reel might be handy, but I would try the cover without one first. You might find that it's easy enough to just pull the cover over the fence and then fold it and roll it up. With a reel you could wheel the cover out of sight or into the shade to protect it, but you'd have to detach and re-attach the straps every time. It wouldn't take long, but dragging or carrying the cover might be easy enough as it is.
If you do eventually decide to get a reel, I've been very happy with the Vingli I got from Amazon: