Glad to know I'm not the only one with hose issues! After using a neighbor's hose reel that uses water pressure to roll in the hose automatically, I invested in one for my front yard. This is the first year my hose has actually been put away properly after every time I water. It really works!
Unfortunately, I've only seen those gizmos for maybe 100' of hose. My backyard takes almost 200' of hose to reach to the back, so I'm still hand-rolling it up into its bin... well, every once in a while anyway. Mostly it stays in a heap or strung out along the patio where I have to water pots every day.
I too was not thrilled with the estimate for an automated watering system... though if we had the money I'd do it in a flash!