The issue with longest road awarding the +2 VP inconsistently occurs when the player with the longest road loses it by getting their road length cut by a settlement being built AND there is another player's qualifying road that takes the crown. I believe the issue is the how and when the program checks for awarding longest road. When this happened in my game, and then the original player retook possession of the longest road title, was re-awarded the +2 VP, but I was still kept my awarded +2 VP. I would upload more screenshots, but only one is allowed.
Edit: This thread now includes the road counting bug as well, where the longest road path is being ignored and counted incorrectly. -Austin