I am having a similar problem. I pumped mine up to 45 psi for 2 up touring, but after 320 miles and 2 days I checked it and it was down to 35 psi. Are the shocks supposed to leak air over time?
I have the same problem .
When i only put 40 psi into the shocks for solo-ride then the shocks keep the pressure for long time .
But when i do put in the max.50 psi and ride two-up , then there is only about 30-35 psi after 200 km ride .
When i do not use the bike ( with the 50 psi pressure ) then the 50 psi stay in there for 2 weeks or longer , no problem .
So it seems to me that the shocks are not able to fight against the max.pressure when riding two-up , their max-keeping is about 30-35 psi when two-up riding .
My BSR and me are " only " 140-145 kg together , that should be no problem .
I complained at the dealer and the oil-licking of the shocks too .
Because there is no service-possibility and instruction from HD for the shocks ,
he ordered the shocks 2 monthe ago and received them last week and will change them on warranty next week .