Shawn,
Unless I am missing something or things at Dynon have changed, when you presently purchase Skyview, the database subscription is included in the purchase price of the unit, for life. For my Skyview database subscription (FAA aviation and obstacle), I pay nothing. Now, if I want to add Seattle Avionics charts to Skyview, that is $99/yr or $199/3 yrs.
I let my Seattle Avionics subscription expire, because Skyview and/or Foreflight/WngX suffice just fine (VFR).
That withstanding, the G796 and Aera 660 units are awesome. But at this point, adding either one would be somewhat overkill.
As you implied, I also use my iPad for additional information and Skyview backup.