thedistinctroom wrote:Generation 1 ended with
Battlestars: Return Of Convoy. This line was all futuristic vehicles and stuff while
Generation 2 begins with present day vehicles. This is where I get confused.
The timeline does not make sense. So, where does G1 end and where does G2 begin? Thanks.

You're making the mistake of thinking everything is in one single continuity. That's
not the case.
For starters, Japan and the US went separate directions with the fiction from Headmasters on.
In the US, Generation 2 was, at first, effectively a "reboot" with repaints of toys from Generation 1. The Marvel comics hooked in on that by having the G2 story begin where the G1 comics left off. Japan on the other hand had made small jumps in the future with each new series, something the US did not do. Simply put, Japan was in 2025 by Victory, while the US was stuck in 2005 (or 1991 in the Marvel comics).
So there are two main time lines, at least. But the main idea is to keep the US and Japan one apart from each other (so you don't get any more headaches).
One more thing: Japan never had the full Generation 2 line: only the Combat Heroes, Laser Rods and Cycles, and Cyberjets were released there in 1995, 4 years after Battlestars ended.