Underwood: I have had a 6 module cabinet for over 20 years. Very well made and not one module has failed since new
SwissKubik Masterbox: I have had 3 single units for well over 5 years. Very well made, programmable and reliable
Orbita: Again, 3 units since about 10 years. Unattractive, well engineered, reliable and a bit more affordable than above two brands
Wolf: They work until they break
If I was to buy more winders today, I would most likely lean towards the SwissKubik.
As to boxes, I don't have anything fancy but I recently purchased a new Delugs Zip Box. Well made, portable and compact but not suitable for large and thick watches.

Photo: Underwood

Photo: SwissKubik

Photo: Delugs