Ok finally made the trip to see both watches. Unfortunately the shop I went to no longer had the Tag boutique. Luckily there was a Tag AD not too far away.
First initial thought: This is why you go see stuff in person. Don't trust renders on websites.
When they brought out the Aqua Terra without even touching it I knew this was in a whole different league. The Omega had much better finishing and honestly looked more like a dress watch than a sports watch. I did look at the Teak dial on a rubber strap and that was more dressed down.
The Carerra felt more like a watch you wear to the office while the Omega felt more like a special occasion watch.
All of that being said The Tag did fit my wrist significantly better that the Omega on the bracelet.
This is a very difficult call. Honestly I've come to the conclusion these 2 watches, although similar, are very different and don't overlap as much as I thought they would for how I would use them. I'm considering buying the Tag now and getting the Omega in a year or two after the gray market get them.
My other option would be just get the Aqua Terra and buy the rubber deployant strap to dress it down sometimes.