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One thing you should do is check out The V Star 1100 Wiki Knowledge Base (link near the top).
Lots of useful info on these bikes that may be helpful on some of the issues you come across.
This is from the Knowledge base.....V-Star 1100 Wiki Knowledge Base - Engine Timing (google.com)
Bet you have bent valves or a busted piston. That gear & chain do not just break.
Chain is fine. The main part of the gear is fine on. It’s just that thin outer gear which appears to be pressed onto the the main one that is damaged.
Me too Chappie......no ideas on that one at all
Something caused it to break, it didn't just fail for no reason. If you turn the motor over by hand & watch the chain & gear, you'll see (maybe) why that gear is made that way. When someone screws up the cam timing & then just hits the start button, things break. I had one in the shop after the local Yamaha mechanics (LOL) worked on it . Removed the cover, turned the motor by hand & watched the cam drive the chain/gear, instead of the gear/chain driving the cam. Had another after the 'mechanics' fucked up the crank by turning the motor backwards to line up the timing marks, jackasses never admitted it either. Sold him a motor with a good crank & took his for parts.