Much depends on how cold your location gets. We also have about 200 ft of hose to use watering daily.
Winding it on the reel with end open, does not seem to allow enough time for hose to completely drain. This was even with having to wind hose uphill to the barn. We still had to put wheeled cart w/hose into heated tack room to prevent freezing.
Last year we did the air compressor thing, left hose lay outside. This worked 99% of the time. Husband made a fixture with a brass hose end on one side, the air hose snap in piece on the other end. We screwed water hose onto air hose, let the air run at least 10 minutes after last visible water coming out. Less “blow-out” time seemed to result in frozen hose. Leave hose ends open while laying on the ground. It still froze a couple times. Once we were able to run hose from house window with hot water, fixed the frozen issue. The other times I just got out the spare hose on the cart, unrolled it to water, then rolled it up again to store in heated tackroom. We put frozen hose in the basement to thaw, then got it out and went back to blowing it out again. No specific reason hose froze those days, it just did.
DO WEIGHT DOWN LOOSE HOSE END!! It will probably flail about wildly as the air starts pushing thru. Flying metal end could hit or break things if not weighted down while blowing hose out. Piece of solid firewood seems to do well for us. We have a big shop air compresssor, so that is a lot of force going thru. BE SAFE!
Blowing hose out instead of winding it up is a huge time saver on cold nights! Wrestling cart into barn and tackroom is not as easy as it sounds either. We really appreciated saving time and work with no rolled hose!!
We considered most of last winter as “not that bad” in how cold it was, moderate snow to deal with. The old horse only needed a real heavy blanket less than 5 days. We will be using the compressor again this winter, see how it goes. I ALWAYS have the backup hose ready to use in the warm tackroom.
We tried the cloth hoses because of their light weight. They only lasted a few days. Being dragged around quickly rubbed holes in them causing leaks. Way too expensive for barn use!!