Not really an insurance thing..difference should be minimal. As I understand it, the 500 and the 750 are the same bike..mostly..same frame..etc..even the same weight..only the displacement is different.
If I trade in my 2016 500 I'll be lucky to get $2,000 for it. So with another $5,000 I am in a new 750. I can get a 750 crate engine for $1300, and probably another $500 in labor to install, so it seems more economical to go that route.
If i go the trade in route, I am probably going softail, road king, or maybe dyna. I was thinking about a night rod, but with the line being cancelled..not sure I want to go down that path.
I think first i will stage 1 it and see what that buys me. My main gripe is acceleration uphill and a few more BHP might make me happier.
"Life is like a grindstone - it'll polish you up or grind you down, depending on what you're made of" - Unknown