Every few months, I question my rep collection. Having sworn never to buy a gen again, I've slowly started rebuilding with a couple of used gens and a couple of highly modded Frankens with gen Rolex movements. I've now identified (I think) which models are keepers and which are not. I will never buy a brand new watch in store again. There are always deals to be had.
Back to reps, who doesn't like having a box full of watches to choose from? Buy one for $358, see if t works. If not, sell. All for $50-$75 loss. It's great.
As others have said, the "getting caught" is in our head. What % of the population are WIS?
Buy what makes you comfortable. Even $358 spent on something that is never worn is a waste of money!