It seems as though this argument between you two started from my comment about using a single cap ship to destroy the defending pirate fleet.

To clarify, I wasn't suggesting that you would use a cap ship to only take out the fleet. After all the fleet is the hard part, so if you took the time to take the fleet out I would assume you would also finnish the job by taking the base.

You also have to consider if you get hit and take heavy loses. You cant just make a move assuming you would be triumphant. You need to wiegh your options and decide which one takes less risk OR pays out more for your heavy risk. Its my belief that if your enemy is cut off by a chokepoint held by a third party. Its in your favor and HIS to take that chokepoint not just neutralize that third parties ability to defend itself. He may have less planets, But that doesnt mean his Units are less lethal. Infact by going on the offensive your taking a huge risk. As your now in his house and he is able to produce reinforcement Units and field them faster then you can replace your loses. Youll have atleast 2+ jumps before any reinforcements reach your Fleet and hell have only 1. This is assuming your opponent isnt a total idiot. Considering the fact your cut off from your enemy. Im going to guess that skirmishes up to the point of cutting off the Pirate Defense Force have been little to none.  Meaning your not losing any form of momentum if you decide to take the Chokepoint. Your creating a Staging Point/Fall Back position for other fleets and incase things go horribly wrong your not totally turned back and find yourself repelling his Fleets from your side of the System.