Other than budget, there are three major considerations when choosing the right watch winder: how many watches, programmability, and watch size capacity. Plenty of single watch winders exist and a wide range of budgets, as you move up in number, the choices get fewer and prices get more expensive. If you already have or are building a collection of automatic watches, a four-watch winder should keep enough ready to rock at any given time, assuming the fifth watch is on your wrist.
Programmability: This may require you to do some homework. All watch winders run on a move-and-rest pattern, simulating the stop and go motion of the human body. That is crucial to avoid damaging watches by over winding them. This simple consideration will accommodate most entry-to-mid level automatic watches. For most watch winders, all you have to do is set the power reserve number for your watch.
Once you get into higher-end watches with more complex movements and complications, you may have to adhere to specific winding directions and amounts. That is why higher end watch winders come with programmable settings. Finding the correct setting for your watch will require cross referencing the watch manual and winder manual. When in doubt, you can always contact the brands directly through e-mail or on social media.
Size: As far as size capacity goes, you need to make sure the winder can handle the case size and band size of your watch or watches. Unless you have an enormous diver pushing 48 mm, or a very small bracelet, almost any good watch winder will work for you. Just check the specs before purchase to be sure.