I have a 2011 Heritage Softail. I have the shocks set up just right for myself. I occasionally ride 2 up. I have heard that it is important to adjust the shocks for the extra load. I have heard that if you don't, it is not good as the additional weight will affect the belt tension (extra weight increases the tension). Without stiffening the shocks the extra weight will create problems.

Since adjusting the shocks is such a pain in the rear, just curious as to what most do? Adjust each time or leave it set as is?

 

You adjust for ride comfort.
If you're passenger is not complaining or your not bottoming out then don't worry about it.

For me even though I ride 1-up 70% of the time I adjusted the shocks for the best 2-up riding and just left them that way.
I eventually about 5 years ago put Progressive 422 RAPs on so now all I have to do to adjust the ride is turn the "Remote Adjustable Pre-load" (RAP) ****.
The RAP **** sits just behind my rear left foot board.