Yes I'm one of those guys who only recently realized the mess of having tablespaces inside the data directory... now I want to use pg_upgrade and it will make things even worse...
Does anyone have a best approach to this problem? Fastest/safest?
pg 9.3.x on win
If you can afford to shut the server down, the easiest is to shut it down, move the tablespaces (with mv, and as long as you stay within the partition it should be almost instant), update the symlinks to point to the new location, and start it up again.