I can't offer much advice regarding skeet guns, and my over-under work has mostly been afield on rabbits, my interest in bird and upland game shooting having ended when my decade-long hunting partner and friend had finally retrieved her last birdie. My use for shotguns nowadays is mostly confined to fighting shotguns, and those mostly as vehicular equipment and for front-door chore purposes at night.
I think your better pick is a 12-gauge 11-87. They're reasonably reliable, and MSRP runs around $783 for the 11-87 Premier Skeet version. Pick up a 21" Remington #29623 Premier Deer Barrel with Rifle Sights and screw-in Rem Choke at vabout $205, and you're almost in business. Get a Choate or Scattergun Technologies 4-shot magazine extension and keep it handy; when shooting skeet or if you go hunting you won't need it, but if your Dad is right, troubles may follow and having the same magazine capacity [eight] as an M1 Garand may be useful. Throw a sling swivel for the buttstock in the box with the mag extension and include a sling of your choice, unneeded for skeet and not common with most hunters other than those after deer or turkey. You should still be under or just over an even $1000, leaving the rest for you to spend on ammunition.
You'll find that the 11-87 wears out the neoprene o-rings in its gas system over time, so either pick up a set of the gunsmithing manuals specific to the 11-87 [also available on DVD] and a couple of sets of the necessary replacement parts, or have a local gunsmith show you how to install them.
If you're so inclined, you could spend the second $1000 on a second identical gun, which could be a spare for you, or a twin for Dad or for someone else who you'd be comfortable with so equipped. Alternately, you could spend half on the shotgun and the better part of $1000 more on a good M1 Garand, which would get you right up in there for target shooting out to 600 yards...and with an 8-shot semiauto rifle, just like your shotgun is.
That may be a minor consideration for most skeet shooters. But there are those who specialize, and those others who are generalists who deal reasonably well with a variety of tasks and disciplines while looking for the one they choose to put more effort into toward skill development.
