I have been using Ubuntu as my only OS for a couple of years now, but from time to time, due to compatibility issues with some software I want to use (mainly games or drawing programs) I have installed Windows alongside.
One of the big reasons I end up removing Windows every time is how much of a hassle is to keep my files up to date in both OS. Art files, documents, videos, stuff I downloaded... making sure the latest version is always available is a bit of a pain that requires a few reboots to move from ext4 to a ntfs partition if you aren't that good at planning ahead.
How would you set up your drive so the files in your /home are available to both OS? Just making your /home partition an ntfs one? Some other way?
Impossible. /home MUST be in a POSIX compliant filesystem and Windows does not have one.
The way to do this is to create a mountpoint formatted as NTFS and then to point the system to look for the directories inside /home at that mountpoint. See ~.config/user-dirs.dirs on how to do that. Set the NTFS mountpoint to read/write, not executable. That way you can watch movies or play music from both systems (Only use a directory that is in a compatible filesystem to execute scripts for Ubuntu/Linux; safety comes first).
So if the mountpoint is
/discworldyou would have a/discworld/Desktop/,/discworld/Documents/,/discworld/Downloads/etc. You can also use this for multiple users on the same machine: set those directories to a group that includes all those users.