1. Yes it is a pain.
2. Yes it does help retain heat and stop evaporation.
3. One person alone can handle it but it can be frustrating.

We have a 24 ft round and currently have the solar cover on. Our pool temp was near 90 most of the summer, but here in the midwest in August our nights start to get pretty cool. We've been in the 50s for the last few nights and our pool temp dropped to low 70s. OUCH. Out came the cover. My husband has a long pvc tube he uses to roll the cover on (like a reel) and then we just carry it to a convenient corner and drop it until it is time to put it back on. Gets junk in the pool, but when it keeps the pool at or above 80, instead of 72, it is well worth it. I can't handle the stupid thing without help, especially after a rain when it gets some water pooled on top. The kids got big enough to help at about 10. If you get in the water with it, it makes the job easier, but we usually don't do it that way.