Playing bj and somehow someone only gets one card

Pit boss says '"you can't lose.play the hand out.if you win you win.if you lose you push"

My friend gets 18 vs 9 AND HITS lol

1)how bad is this mathematically? I think it's horrendous
2) I had 33 vs 9. So I wanted to split figuring the more hands the better on a free roll. Pit boss wouldn't let me split and free roll the hand though. How much of a better play was splitting if he allowed it vs hitting?
3)this one is closest I think.

Hypothetically 17 vs 7. I think it's a hit bc 4/13 th of the time you push out of the gate anyway (plus some times they make a multi card 17)

Would hitting 17 vs 7 have been correct on this free roll?

According to my fancy WoO blackjack workbook I copied from his YouTube video, when a dealer shows a 9, he busts 23%, gets 17, 19, 20 with 12% each, gets 18 35%, and gets 21 6% of the time.

Your friend pushes 12% + 12% + 35% + 6% = 65%, and wins the other 35%

Your friend busts if any card 4-K comes up, which is 10/13 of the deck, which happens 77% of the time. We can stop at this point and note that best case scenario he could win 23% of the time after hitting (which overstates the actual odds since he could hit and make a higher pat hand and still lose). Thus, standing is the correct play.

For 17 vs 7, you are pushing 37% + 14% + 8% + 8% + 7% = 74% if you stand. The odds are a little closer, since the odds that you bust after hitting on a 17 is only 69%, but you can still lose after hitting to a higher pat hand.

Look up free bet blackjack on wizard and the strategy for the free hands to get a pretty good idea.

This illustrates the importance of always screaming for the floor if there is any irregularity in the deal. If the floor is called, you might not get a freeroll, but if the floor isn't involved, you certainly won't get one.

Just the other day, 3rd base didn't get dealt in. (Dealer shows an Ace.)
I say, "Call the floor."
He says, "No, I don't want to get the dealer in trouble."
"She won't get in trouble. It happens all the time. Look, she has your Ace."
"Do you want me to call the floor?"
"YES!"
He doesn't call the floor. Dealer blackjack.
Next time I'll just do it.

Why didnt you call the floor?
No chance in hell the pit boss doesn't get called if I'm at the table

Yeah, actually dealer herself should have called the pit boss.

Last time I called the floor on someone's else's behalf the floor ruled against me (they know I'm AP). I thought our chances were better if the whale did it.

that's fine but once he didn't you have to call them

again, third base was a happy loser. without him on my side, floor had permission to do nothing. the dealer got tired of waiting for us and just flipped her hand over.