I've had my pool about 7 years, and have also struggled in varying degrees. It's always easier with 2 people, but I usually find I'm doing it by myself.
I think I may have been closest to what I want this year.
- I connected all the plumbing and filled the pool up so the cover had extra slack and the extra water was sitting relatively flat.
- Then I put a cinder block on the cover closest to where I was siphoning from. This gave a nice deep area for crud to gather.
- To siphon off, I have just used a pool hose I already have and got it started with a shop vac. I keep it oriented below the water be wrapping it around a snow shovel and place it like I want in the the pool.
- As water was moving, I occasionally moved crud around the cover towards the cinder block pit with a hose.
- When I got most of the water off the cover (never ending, becuase my cover is as old as the pool ans is starting to seep water in both directions), I dove my arm into the nasty water to get the cinder block out (note for next year: tie a rope around it).
- I then untied the cover and took it off like a taco shape. This allowed the weight of the remaining water to be distributed rather than contained at a single heavy point. I could relatively easily just slide the top off the "taco" off relative to the bottom.
This year, the problems I encountered where having to dive my arm into the nasty water to retrieve the cinder block, and dealing with the wind while removing the cover. Since I was working along (poor planning on my part again), I had to quickly work around my 24' pool. At a crucial point when I had it oriented like a taco and the pool was clear, the cable was stuck on an upright at the other side of the pool. I left the taco to loosen the cable. In that moment, the edge of the taco slid into the pool and started dumping the winter's worth of decomposing leaves into the pool.
Next year, I'll get even closer, or remember what I "learned" in previous years.