as a general rule for any fruiting plant if you want more but smaller fruit (which is sometimes handy in a domestic situation) leave both/all fruit on. If you want a bigger fruit cut one/some away.
I'd go for two smaller ones myself, pick one, eat and enjoy then couple of days later pick the other. I wonder if they will both ripen up at the same time
watch out though, getting the rough end of a pineaple can be nasty
this one got quite big