Carter, I think you are correct to suspect that this situation is problematic (was this Andy's idea or yours?). Here's how I see it ( and someone tell me if I'm way off base):
*You are allowed to keep two first rounders (or any number from a single round) if you were shrewd enough during the season. It seems wrong to then make you give one of them up just because they both happened to be drafted in the same round. Our solution was that you'd lose the next available round automatically as sort of a compromise for having ended up with two of the same round. Otherwise, people would be even MORE hesitant to trade if they worried that they might have two of the same round that they wanted to keep.
*What you are proposing seems bogus. You can either (a) keep David Wright (b) trade David Wright and open up a first round pick for yourself or (c) trade your first round pick and give up your ability to keep David Wright all in one fell swoop.
*I don't see a legitimate reason why you should be able to trade your first round pick and then just let Wright magically fall to the second round where you can keep him. That just seems wrong and against the spirit of keepers. You would then essentially be getting something for nothing (ESPECIALLY since you don't have a second rounder on your team right now so you wouldn't be bumping anyone out of that spot).
*We ARE going to need to develop a system for what happens next season if you want to keep "old keepers" and "new keepers." Will the "old keepers" just supersede the "new ones" and just get added on in lower rounds? I'm not sure that this is important now, though.
Other thoughts? We need to develop a wiki of some sort to keep all the rules straight. I think I'll create a Google document that can then be edited as needed.