Based on the definition and what I've seen....yes to both, definitely the tow rig though. For the $30 a year and as much as I've gone out, it's worth it (but I don't need a tow rig).
Yes, because you would be "parked". However, if you tow up there you really only need the one pass and display it in your tow rig. In years past, the annual pass had both a wallet card and rearview mirror placard; that way, you could wheel and still have a pass. Now the new passes don't have that but if they ask you just let them know you have one in your tow rig.