I think Jared misunderstood Tom's post. I think what Tom meant was that because he was getting the "flip not supported" message, he was therefore not allowing it to get to the point (time-wise) where flip would be expected to happen since the message was telling him it would not work so it was not safe to allow it to get to that point unattended.
I was the one that he was working with so I know he had the degrees past meridian set to a positive number ( 2 degrees if I recall correctly).
I wonder if this is not an issue with TheSky6 and the Paramount as opposed the TheSkyX (which I am using). I know this is similar to the issue I had where the mount was not sending pierside information and therefore giving me that message. I corrected that by inserting and activating "cangetpierside" property in ASCOM profile explorer. With the new driver this can be toggled from the driver dialog by selecting "pointing state". My understanding is that Tom does have this set properly in the new driver and has even checked it's state in Profile explorer.
Since it works for me with the same mount and driver (and, as far as I know, settings) I have to wonder if this is not something specific to TheSky6 vs TheSkyX as that seems to be the only difference between his system and mine as far as I know. The mount and even the camera and focuser are the same in our two systems.
I wonder if anyone else is using the combination of TheSky6, The New Driver, and SGP? I would doubt it but if so we would like to hear from you! TheSky 6 is pretty old, that last update was in May of 2009....
Might be time to have a look at Tom's logs to see what is triggering the message.
Also, FYI Tom is a very experienced imager and knows far more about software than I do so is not too likely to make dumb mistakes except where related to not being totally familiar with SGP/PhD (since he is relatively new to SGP).