I'm not sure why people act like it takes Jiraiya a year to enter SM. Bunta or Ken can buy him enough time to enter it. It took him from page 2 of the manga chapter to page 12, which included non-stop action, to enter SM.
To give him trouble entering SM, you need to be able to be someone like Kakuzu who can attack with high level abilities from multiple angles, or have extremely high levels of speed to get around the summon. Kisame doesn't quite have that in his arsenal. Otherwise his toad summon buys him the 2 minutes it takes to enter SM and he goes from there.
So the scenarios really don't matter here other than how long it takes him to put Kisame down.