Well I'm unloading a few of my watches to fund my gen purchase, so I'd say there's nothing wrong with that. I also like the idea of multiple watches but I noticed that the more watches I have the more that I want..... I figure that I'll sell down to about three watches and then work up to get a nice dress watch.
As far as the 14720 if you like it get it. However it seems like you have some reservations due to the lug holes. Spending that kind of money for something that your not in love with is silly in my mind. Thing with spending several thousand dollars is I expect perfection, heck I want perfection when I'm only spending a few hundred dollars. Maybe if one small thing bugs me I'd still go for it but if it's something bigger or more than one thing I'd say skip it. Get a rep and mod it to a fantasy of exactly what you want and save a bunch of cash. Could buy the 14720 and drill lug holes and be happy. But with a Rolex you have to wonder how much longer you can get parts to service it independently or send it to a RSC. And if you send it to a RSC with lug holes what are they going to do? Refuse to service it? Make you get a new mid case as part of the service? If lug holes are the deciding factor then I'd say skip it, you'd buy it and not be happy, there's no need to chase water down the drain....