On the "gen is an investment" and such, I am very skeptical. Yes, you might have seen it for sale at a higher cost, but you won't be able to sell it at that amount. You essentially have two options: A) Sell it to a shop (Watchfinder here in UK, or any equivalent elsewhere) which will pay you peanuts compared to what they will put it up for sale. Or B) Sell it in a forum or Chrono24 or similar, where you will have to price it down compared to any shop you have seen (as the majority of buyers will prefer a shop because of the warranty and safety you get, especially when talking about big figures).
In any of both options, the investment is not that much profitable, unless you are talking of very specific watches, like selling now a 1675 that your grandad bought new in the sixties, or some of the old vintage subs. But buying a 116610LN or any other steel Rolex brand new at AD price is definitely NOT an investment, you might get better returns just buying any normal finance product instead of a watch.
On the Gen vs Rep... I must say I get the same buzz when I buy a gen than when I buy a rep. And it goes away equally fast, so I'd rather spend $400 once in a while than $4000 with the same frequency. If I was a billionaire, if money wasn't a problem, if, if... well, if that was the case I wouldn't probably be posting here in the first place, wouldn't I?