Mikey, sorry to take so long to get back to you - my wife thinks that Friday nights should be used for other than cruising the gun boards - I don't know where she gets these ideas.
To answer your question, I am going to assume that you want an under / over, it must be an actual trap gun, and that you want a new gun.
The new Wholesale catalogue lists a Browning Citori Target XT Trap for $2,519.95 with your choice of 30 or 32 inch barrels. An excellent gun, but a little above your stated price. I consider it to be generally in the same price category, you might feel differently.
The same catalog lists the Beretta 686 E with 30 inch barrels and an adjustable comb for $2,399.95. Again, a little higher in price than the Select, but only $140 more than the Winchester equipped with an adjustable comb. I like Beretta competition guns, so I may be prejudiced here.
Saving the best bargain for last, check out The Shooting Edge in Calgary for their line of Fabarm shotguns. They offer no less than 5 models of trap gun in your price range, starting at $1,949 and going up to $2,359. The adjustable stock Gamma model is right on your price point. These are nice guns, and there is a world of upgrades and options listed, including extra barrels. Check out their web site.
If you are a real Winchester fan, forget the new guns and find a Winchester 101 trap model. There are many minty examples out there if you look, and you will save a few hundred dollars.
Whichever shotgun you choose, it must fit and feel right to you. The balance, the grips, the pointability, and the sight picture must be compatible with your physique and perception (an adjustable stock helps, unless you already know the dimensions you are looking for). You cannot get a feel for these issues by reading a catalogue - you must handle the guns. Handle as many as you can, swing them, throw them to your shoulder repeatedly, and trust your gut instincts as to what feels right. Who knows, it might even be the Select - but I doubt it.
Sharptail