The disadvantge is spending a $1000 and you may end up not liking hunting at all, but it sounds like you may have already been hunting with your friend.
The other issue is if you like hunting, you may want to try other game, for which an O/U may not be ideal. You also say you want a wood stock, but if you plan to bust brush and you want the wood stock for looks, briars are hell on a wood stock. Personally I prefer wood stocks too, but I dont hesitate to put my gun ahead of me in the briars. That inlcudes my O/U's. I am not out to tear my guns up, but hunting is hunting, no safe queens in the field.
If I was going to buy just 1 gun that was for birds first, then assume Skeet and sporting clays too, a semi-auto with a 26" barrel is a great all around compromise. You can get longer and shorter barrels for it later based on hunting geese or small game.
But a 26" barrel can do it all, espcially if you invest in some quality choke tubes. Look at Remington, Beretta, Benelli, Winchester.
A Remington 870 with a 28" barrel or Benelli Nova are great guns for tearing through the field with, and there are tons of barrels and accessories for both.
An affordable new O/U is the Beretta white wing, Shop around and you can find it for $900 new. I have one and use it for everything. I bought a nice brake down SKB case for it and it travels in the truck and on the plane easy.
Remember, field guns are carried a lot and shot a little, weight is an issue. Lighter is better in the field but lighter means more recoil too. That is where a semi-auto like the Remington can be nice, not too heavy, and less punishing on the clay course.