Perhaps I am not destined to be a collector; to feel this way about more than a 3+1 collection could easily grow maddening. I also feel that this will require me to feel a similar sense of value and enjoyment from each watch; to ensure that I have little cause to favor (or not) one over the others.
I learned a long time ago that 4 seemed the be the most watches I could have an easily keep them all running and rotate through them with a great deal of regularity. That hasn't stopped me from going beyond that number. I've just learned to live with resetting watches if I don't wear them for a while.
I know some people like the idea of watch winders, but I don't. To me they only make sense maybe if someone has an incredibly complicated watch. Years ago I asked a watch maker his thoughts on watch winders. His response was, "When you aren't driving your car, do you leave it running all day long? No? Then why have your watch running all the time if you aren't wearing it?" His main point was why should one put wear and tear on the movement if you don't have to. Now that wear and tear is probably very minor, but I can live with resetting my watches when necessary. However, if one is going to use a watch winder, it should be a very secure safe set up. Years ago, someone relayed a story about their Vacheron getting damaged, when it fell off of a winding unit and part of the winder continued to hit the case for the next day or so until he discovered it. There were some nasty scrapes in the case from where it had repeatedly made contact.