So I swapped out for a 242 using the same speedo gear that was in the 249. Never leaked in the 249 now I cant get it to stop.

Tried RTV twice and the original o ring looks in decent shape.

Is it true the oring size is
1 7/8-inch Outside Diameter (44mm)
1 9/16-inch Inside Diameter (40mm)
3/32 Wall Thickness (2mm)

I am gonna try to get a new one. Does anyone else have any recommendations?

 

Try a 1/8th O-ring with an 1 7/8 OD and see if it slides in without too much effort. That will give you just a little more compression against the bore. It may work, it may not, but it's worth a try.