For $1000 you should be able to find a used 20ga Beretta O/U easy, unless recoil is an issue and that is the deciding factor on getting an autoloader. For an auto; Beretta or Benelli is a toss up and I would buy the one that fits you and points well.

I owned 28ga Wingmaster and it is a fine utility stick and I don't mean to unnecessarily contradict 2many but ammunition is harder to find and more expensive particularly when shooting clays.
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In the legend of King Arthur, the Fisher King was a renowned angler whose errant ways caused him to be struck dumb in the presence of the sacred chalice. I am no great fisherman, and a steelhead is not the covenant of Christ, but with each of these fish I am rendered speechless.