Hmmm....that is a very good question!! TBH, I don't have much experience with shortner nights working in our favor, so I'm not quite sure what to say! I've no doubt that some mommies have taken that route and have found that it works, afterall it is so individual, but it is not a route I would have ever taken intentionallly.
But I think I see where you are coming from. I remember once with my DS it happened we were at the ILs for dinner and got back late. He had a late CN in the car on the way home and when we got home I put him in to bed fairly quickly, he went down like a dream, slept a long stretch that night and I think only woke once.
What I learned from that experience is it's not so much a shorter night that's better for him, rather it was having his last nap end fairly close to bedtime, therefore having a short A time before bed. And this rule has almost alway held true. When he is unable to handle the proper A times until bed, and when he is OT, his nights are ALWAYS better with his last A time being shorter.
So, in a sense you are probably onto something. I think you are right thinking that if he can't handle a long A to bed WITHOUT having a catnap, then slotting in the catnap and doing a later bedtime would be the way until he is ready to drop it.
And as with all transitions you could alternate 2 and 3 nap days - when he takes 2 good naps and is well rested, skip the CN and go for an early bedtime, and on days where the CN is necessary, do a later bedtime.