ICT Billet has a variety of those things as well other handy LS swap doodads.
Everyone says that, but it never happens.
I use sealant on NPT, pretty sure it's always required. Do not use sealant on male AN to female AN.
There's no such thing as an ORB hose connection, I've never seen one anyway.
If you've never made an AN PTFE connection, let me tell you it's no fun at all. The push on AN connections and hose will make your life easier and be fine for an oil cooler. (Heck a hose barb and a clamp would probably be fine too.)