Does Version 2 work on Windows 11?
Unlikely...perhaps partially. Fences4 was designed to work with W10 and W11. Fences 2 worked on: Windows 7 / Windows 7 x64 / Windows 8 / Windows 8 x64 / Windows Vista / Windows Vista x64 / Windows XP / Windows XP x64.
What is the cost of an upgrade to version 4?
I'm not 100% sure about a] whether you can upgrade from v. 2 to v. 4. softwarewise, and if you're eligible for that upgrade and b] the price for an upgrade depends on single or multiple licences.
https://www.stardock.com/products/fences/