A consistently designed well-documented system is probably easier to use, all else being equal.
Obviously I'm an outlier, but if I need some software on FreeBSD, I'll contribute a port. Most of the time, it's almost trivial, and it's only with very obscure (maude is one that I'm currently working on) or newish (RethinkDB, which isn't written in a super portable manner - it doesn't even use pkg-config and has a hand-written configure script!) where there's an issue.