There's never a guarantee that you win one, of course you need some luck, but we should be contending well before 5 more years.I think there is a genuine chance that we don't win a flag for another 5+ years. Not to say we can't or won't contend - but being in the discussion doesn't guarantee anything.
Probably the biggest piece of the puzzle we're missing is maturity and experience in a successful side. You look at what Collingwood are doing at the moment, it's off the back of leadership and valuable contributions from guys like Pendles, Sidebum and Elliott. When the heat is on, we don't have those mature heads to steady the ship on-field and say "right, this is the play". You look at that coast-to-coast goal that Collingwood scored to sink Essendon. Pendles was interviewed afterwards and revealed that he knew most sides would expect a long kick up the corridor, so he told Moore to break left or right if he saw some space, knowing that Wright wouldn't be able to keep up with Moore on the break. You know what Carlton does in that situation - Doc, Weiters or Newman launches a barrel up the guts and we hope that TDK flies and clunks a massive mark.
Now maybe we can add a player or two to assist with that, or maybe we can get a big collective push from our talented players to get us to the top in the next couple of years - but it is equally possible that we're just "thereabouts" for another 4-5 years, making finals, winning some, but ultimately bowing out in the first couple of weeks of September. And it might then be the kids that we draft over the next few years - the ones who get the opportunity to learn in an environment where finals are a minimum expectation, from guys who have played in big finals for a few years - who get us to the next flag, while someone like Cripps might be battling for fitness and missing out.
Our list is good enough to contend. If any other team had had our injuries this year, they wouldn't be top 4.
That's not to say we're perfect, or don't need to improve. But you use Collingwood as an example, if we had had their luck this year, we'd be 2nd.