For MY 2017 health plan:
Max out of pocket for MY HDHP plan is $5,000. Anything over $5k is covered at 100%, with no deductibles, no co-pays, etc.
Max allowable contributions for 2017 is $6,750.
For my plan there is no way to max out HSA and still be out.
As long as my plan doesn't change, I will always have money left over.
Best case scenario I'm banking all $6,750 each year.
Worst case scenario I'm banking $1,750 ($6750-$5000), and that's before any RoI kicks in.

I get that may not be a situation for everyone.
According to this website: [Link: shrm.org] some plans may have family HDHP max out of pocket at a whooping $13,100.
With max allowable IRS contributions of $6,750 you're absolutely right, you could be in the red.