Effect of MisMarked Damper +5 degrees?

Generally bearing wear is a sign of oiling issues. Not timing. Loss of bearing crush without showing wear on the bearings could be timing. I'm not sure what crank you used or what the clearances were originally. But if a few bearings were worn I would be suspect of the journal finish on those journals rather than the oiling system as a whole. If you crank was simply re-used you will want to make sure there is no taper and the clearances are right. The typical stroker setup with closed chamber heads and pump fuel will like less total but the same or more initial timing. that has to do with the way cylinder pressure builds as the mixture burns and the angles of the rod and crank. As your static ratio is a little low (again, IMO) you never would be near the detonation threshold nor would you have hot spots leading to pinging. So there wouldnt be much of a loss with more timing. There's extra "room" in the chamber and loss of pressure that regardless of what you do it would run. That's more than likely why it was built just that way. More room for error without damage. If you've never had the engine itself dyno'd you might want to save up and have it done. You might be surprised at where the power peaks really occur. I think the torque peak's lower than your convertor stall.