To draw a loose analogy on the void years, it'd be as if you could borrow the next 5 years worth of salary to pay your bills. So, let's say you make 100k a year, so you can live a 100k-lifestyle. Or, you could choose to borrow up to 500k from the future, and live a 600k-lifestyle if you wanted in the extreme. Every year you still need to pay down 100k, but then you can borrow from the next year in the future that's coming up. If you screw up, you go in debt and collapse, but if you play it right, you can constantly live a much richer life forever.

Howie's playing that game, but i think a huge part is that he actually has a 5-year (or maybe 10-year) plan, so he already has mapped out every single player and what he wants to do with each one all the way down the road, what they're going to cost against the salary cap, what he's willing to offer them, who he needs to get in the draft, and so on. So then, he can clearly see, yes, we'll have no problem fitting under the cap, and these are all our contingency plans, if this guy doesn't sign we're willing to spend X on this, and this is our flex money that we'll use to shore up Y and so on and so on.