Be careful with port grounds: current can only flow in closed loops. If your DC load uses another port ground conductor than the RF input port, simulation will fail.
If your layout is essentially single sided, with all the backside as one large ground, you can use an infinite ground boundary in Momentum stackup (see pictue). That is recognized by Momentum as the default (implicit) ground reference for all ports.
Regarding port calibration, TML seems to fail on your port 1. Most likely that is because you have specified cond2 for ground and there is no cond2 ground drawn below the calibration line. For this explicit (drawn) ground layer, I would switch off TML port cal. If you use the infinite ground boundary instead, TML cal should work fine.