It really is up to you and your habits and the time you have/feel you are using up.
I have plenty of watches that has no date so adjusting it is pretty simple and easy along with a quick wind (20-30 turns). It used to bother me but not anymore, it probably takes an extra minute or two out of my day (which I do maybe once every 2 weeks to a month)? So no big deal for me but I did use to think the same way as you hence owning several winders (though some of them I did get for free with the watch). So i don't think you are overthinking it especially if you live in a fast paced world. I do still use my winders for other watches I just like having wound anytime I need it like my Monaco is my activity/wherever I go watch, I like it wound whenever I just want to throw it on in a hurry or feeling lazy. If you go the winder route, just make sure you have a good winder and you're good to go.
It also helps if the watch doesn't have a screw in crown, makes it much easier to wind and adjust. I figure for a handwound watch I would want it to not have a screw in crown so I can wind on the fly before the power dies, just would be less hassle.
I tend to rotate three watches at a time though but most are automatics so I seldom adjust and wind them. I also try to put a Daytona in the rotation, it has a 72 hour power reserve so it can be worn every third day. I also switch up watches twice during the day depending where I go at night, so again it depends on you and your lifestyle.
I've also gotten to a habit that sometimes when I am waiting or just relaxing, I would remove my watch and wind it a few turns just for the heck of it (also to keep power up).
Not really sure if that answered your question though.
rfx45
as someone who rotates your watches, what's it like having a hand wound? Surely it's irritating when you haven't worn it in a while, and first you have to wind it up and set the time, knowingly that you may only wear the watch again in three days or something? Or do you rather rotate by wearing the same watch for multiple days in a row then move onto the next? I'm looking at birthday presents to myself again, and there's some nice pieces which are hand wound, but I've really fallen in love with automatic movement, and just putting it on a winder until next wear.
kickhead23
Nice fam. That's my favorite watch out now.
