Generally speaking, I find that when I find myself asking the question, then it is time to consider making a move rather than "well wait six months" and see then. For whatever reason, the idea of a change has crept in and unless a new model has been announced and a roll out date set, I consider moving ahead once I sort my needs. A million things can happen, I try to work things that need to be worked and leave the future to deal with then.
That said, I have never own Android. But I have moved from an iP6 to an iP7. I initially poo-poo'd it as just another phone in 6-garb and why bother? Circumstances changed, I made the move, and I must say that I find the iP7 to be a wonderful upgrade from the 6. Not in any 'magic' way, but it has a nice heft (with a Spigen case, glass protector, and Steelie magnet), is very responsive, is rock solid in performance, bright, updated regularly by Apple, and really just an all around nice unit. On the headphone jack debate, I don't miss it. I cut the cord for the most part, there is a dongle if I want the plug in, and I can count on one hand the amount of times I have listened to audio and charged simultaneously (YMMV). The Apple ecosystem has all thee Apps I need and even then, my primary work machines are Windows boxes and I don't find that I am missing anything. I do have a Mac Mini as well, but it get very low use compared to others.
I won't slag on the Android world. It works great for folks and has some nice devices. I would just never consider going that direction (for now) as there just isn't a need that dictates that change.
So I say knock yourself out one way or the other. If you're flexible enough to make the jump to Android then you can't go wrong either way.