On Plugin 1 have an extra bar and un-check ending
On Plugin 2 un-check count-in
In the DAW the change is on bar 33 so you set the volume automation to turn off on bar 33 on Plugin 1 this allows fine adjustment so you get a seamless join.
Plugin 2 is set to sync start on bar 34.
The DAW has a 2 bar count-in offset so you have 2 count-in bars before bar 1.
I have the same part marker on bar 33 of Plugin 1 as I have on bar 1 of Plugin 2 so it will play a fill going into a post fill.
You need an extra bar on Plugin 1 because it cuts notes off too soon so you don't get a seamless join, it was mention to PG a few times but it looks like they haven't got around to it yet.

Watch: https://www.dropbox.com/s/afmd6c08dmlaxd5/BBPlugi-Over-255-Bars.mp4?dl=0

Zoom++