The fitting that goes through the transom to the drive broke off and dumped all the drive lube in the bilge. Does it unscrew out of there? What is the fastest way to fix this. Headed to Poker Run tomorrow!

If it is a plastic fitting, all you should have to do is push the locking clip in and pull it off.

Can the piece that comes through the transom be replaced with a brass fitting?

Well I was able to push and clamp a hose onto the straight fitting coming through the transom for now. Seems to be working in the driveway ok.