I found the source of the water in my bilge, thanks to advice and guidance from Zacs.

The fitting that the drain plug in the transom screws into is leaking. Water is seeping around the screws and bottom of the fitting. I pulled it out and looks like the caulk has deteriorated. The fitting looks in good shape.
Im thinking all I need to do is put a bead of silicone caulk around the fitting and screws and put it back in.
Is it that simple? I cant see what else there would be to repair and the silicone should create the bond/gasket and seal out the water.
Any advice is GREATLY appreciated.....

I would get a new garboard plug kit they are less then $10 and put it on with 3m 4200 as the selant. You don't want 5200 as when it needs changing again you'll never get it off.

Yes, its that simple, but make sure you use 3m 5200....it does come off if need be, I changed mine this year..Good luck

uh oh, 2 conflicting opinions....I need some more!

5200 is the shiznit.

5200 is an outstanding bonding/sealing agent. I would use 5200. It is a PIA to get off though like stated above.

Yes, its that simple, but make sure you use 3m 5200....it does come off if need be, I changed mine this year..Good luck
Yup//// 5200 for sure.

Thanks guys, huge help.

the key is that you get all of the old stuff cleaned out before you re-seal. scrap/grind until you get it bare, wipe down thoroughly with acetone, re-seal with 5200, then put the garboard plug assmbly back. you may want to drill out the screw holes a little to. be sure to fill them with 5200 as well.

Another vote for the 5200.

i used the 5200 last night,sanded, acetone,
wasnt sure if i should load up on it or create a clean bead along the seam. So, I did sort of both,and put it in the screw holes.