Stupid/Misleading government ad to encourage 25 to 34 year olds to sign up for Obamacare

Either the Obama administration is simply misleading or this is more evidence that they don't know simple math.  Of course, both things might be true.

This ad for 25 to 34-year olds implies that there is a fifty percent chance of them having to pay at least $500 in medical bills over the course of a year.  In other words, the expected medical bills over the course of a year are at least $250 (it would be more useful to simply state what the expected bills would be).  In any case, the cheapest state insurance for a 27-year old under Obamacare is $142 per month, with most in the $200 range per month (see chart below).  Could someone please explain to me how this section of the ad justifies the statement "I should really get insurance"?

Of course, the problem is even worse than this because if a young person does get hit with that $500 insurance bill, the insurance company isn't going to have to pick up the entire amount.

The reason why insurance is such a bad deal for younger people is that Obamacare is purposefully set up to transfer money from younger to older people.  Younger people pay much more than what they would pay under true market insurance rates so as to subsidize and lower the prices for older people.