Wow, your questions are so many of the same ones I had.
You're supposed to buy a special lube, is what I was told. I could never find the one that was suggested to me, and I meant to write in again, since they have one at the pool store I saw yesterday that says it's to lube those o-rings.
Are you using Wal-Mart bleach only? Or was it just that one time? You should be buying concentrated bleach in bulk containers, or it's going to cost you a fortune to clear the pool. Our stores here sell 10% bleach refills of 2-1/2 gal. containers for just over $4. It goes a lot further than regular household bleach (sorry if you're already buying that and I missed it).
I used that same leaf gulper you posted the pic of.. A few times it seemed to not work well, but most of the time it was great. Cinch the bag down TIGHT and make sure the little clip is pushed down completely tight, or you risk it coming off and releasing a cloud of leaves into the pool. It doesn't pick up much dirt (I guess it may have a different mesh than mine does though) but it's great for leaves. The trick seems to be to get the right angle on the pole to keep it running along the bottom. And having good water pressure. Empty it often enough, or else the bag is more likely to pop off (ime). And it's really nice if you can have someone else around to turn off the water so you can fish it out and support the bag without water splashing in your face but ... I usually turned it upside down and wedged it at the side of the pool so the bag stayed in the water (too much weight) - upside down to keep it all in, then went and turned off the water. Sometimes I cleaned it and just left the water on, but I usually got a face full of spray every time I tried that. And not knowing what ick the water might pick up, I'd rather not.
Sorry if any of this is already addressed, I was just waiting to see if I'd get an answer on my questions.