I haven’t seen this specific question addressed in a FAQ or post after searching but I may have missed it.
Does the lifetime Plex Pass subscription include lifetime DVR scheduling service?
IE I pay once for a lifetime Plex Pass and never have to pay again for the DVR scheduling service?
The EPG data that Plex uses for the DVR feature is included as part of the DVR feature, which is part of the Plex Pass feature. You do not need to pay for the EPG data as long as you have a Plex Pass.
So the short answers are: 1) Yes, and 2) Yes. 
[corrected - I mis-read your second question, oops.]
@sGarver said:
So the short answers are: 1) Yes, and 2) No. 
Sorry, confused. Which part of my question has a ‘No’ answer please?
sorry, I goofed and now corrected my post above.