My son in law has an 1100 vstar classic, he said it starts just fine on the first time, like morn or what ever, rides , and then if he stops and trys to go again, he has to crank and crank and finally it will take hold and go, I did not know what to tell him , any ideas??
I wonder if it would help to choke the hot engine. If it does not flood and starts sooner that might mean it is to lean. Sometimes happens when we change exhaust. Make sure air filter is OK, Maybe run some Sea Foam carb cleaner through it. Half a can to a tank of gas. Desperation moves but you might get lucky.
My 1100 starts just by hitting the starter button when hot, I have the Maxair predetor kit and aftermarket exhaust. What kind of mods have been done? It sounds like it could be flooding. Float level off, carbs needing sync, valve timing off, just a couple of thoughts.