there isn't a good and solid answer to that
on one end, putting the watch on a winder puts unnecessary wear on the gears and watch in general especially if you aren't going to wear it for months or year and it's just sitting in the winder
while others say the oils are sophisticated and advanced enough these days that it can withstand a watch being wound or worn for year on out, plus you don't want the watch to just sit on the oil without it moving or else it kind of builds up, but then others also argue that oils are in an advance state now that it may not be an issue anymore these days (?)
there is also a risk of breaking the crown when winding the watch manually, odds are low but it happens if you manually wind it every other day or once a week and you aren't the most careful person, yo can break the stem and it'll cost a lot to fix while when in a winder, it's just going to stay wound
the right answer is likely in-between, if you have a 2-3 watch rotation and actually go back and forth and it's a convenience then go for it, if you are the type that just want it there so that when you want to wear it in a month or a few months later you don't have to adjust it, then you are probably better off removing it from the winder and set it aside and just wind it and move it around once very month or so
it matters on what watches you own too, some complications like perpetual calendars are b*tch to set so those could actually benefit from sitting in a winder when not in use
winders matter too, there are some cheap ones out there that might cause more harm than good to your watch, some watch can only be wound going counter-clockwise or vice-versa or bother ways, if you have a cheap winder that only goes one way and the watch can only be wound the other then you are just putting wear and tear on the watch
in the end it is up to the user once you know the pros and cons of each