I'm replacing the plastic fitting that is on the side of the boat that the livewell drain hose connects to. Do I need to put silicone or something around that to keep it from leaking?
These fittings don't ever leak much if installed correctly.
As I noted... its never a bad idea to add some sealant. But the sealant is to stop drops per hour. Proper installation is to prevent gallons per minute.
I replaced all the plastic thru-hulls on my SeaRay last year with SS ones. They were all above the water line. I would not use an adhesive sealant like 3M 4200. Just use some silicon which will last forever. And if you ever have to remove the fitting in the future you'll be glad you didn't use 3M 4200.
Edit: Whoops I see your already done. Hopefully you just used silicon and no adhesives.