Well it would actually be a loss for the gen makers for me. Several of my reps have led to the purchase of gens. There's probably a few more that I have that will also get replaced with gens. Without the reps to try out and grow on me that might not happen anymore.
I fall into that one as well. Have a couple gens but there's no way I could justify spending what I'd really have to spend to get all the ones I'd like (couldn't afford that anyway)
Hmm I don't know. Could go either way if you come clean and tell him. I'm sure that there are some gen collector's who are closet rep collectors as well (come on let's face it whether gen or rep most of us can only support the habit so much). Sounds like he's got some reps as well. You could either come clean and see what happens. Or buy a gen Skyland (not a bad gen to buy anyway and not all that expensive) and that way the watch that was presented as gen would be. You'd then be free to open up the conversation about your other watches being reps.
I used to feel the exact same way about the PAM's until I got a couple. Now there's 25 of the damn things in my watch boxes. You might look over the IWC reps. I've got an Ingy, a 3717, and a Cousteau Diver and love all three of them.