Well I can give you a farmer's viewpoint but others on here are better placed to talk about silage vs hay from a smallholder perspective.
Hay - needs 3-4 days good drying weather. Needs more drying than silage and quite a bit of expertise to make good hay. Bales are lighter than silage and much easier to handle. Hay is also more versatile to use.
Silage - some farms do make it within hours but we usually cut one day and bale the next. We like it as dry as possible and have our own hay-bob so we'll give it a couple of woofles to help it dry. It is much more forgiving than hay; if it's dried a bit, doesn't have an soil in it, is wrapped very soon after baling and you don't puncture the bag then it should be ok. The bales can only be moved using special equipment (so you don't puncture the bag before you are ready to use the silage.) Once opened, the silage will become less appetising very quickly. Cattle need to eat it up within a couple of days really, sheep will probably continue to munch on at it for 3 or even 4 days. Beyond that nothing much (except a Fell pony, perhaps) will touch it. You have to dispose of the used wrap (which will smell like cat wee for some reason.)
The standard large round bales of silage will feed approx 22 housed suckler cows for 24 hours, or 50 hill sheep on the hill for 4 days. Smashy I think you only have a very few sheep so you will need other smallholders to tell you how to use silage for small numbers. You could always make it and sell the bales in the winter, or swap them for hay.