o.o what an IDIOT! HAHAHA my coworkers are trying to figure out what is so funny! This puts both a smile and a look of fear on my face

Answer to #1: no

Answer to #2: Emphatically NO!! And he can't have any more cotton candy.

Comment on #3: Aren't there always??

Not sure how this "game" is played. The usual way similar games work is that the carney demonstrates tossing in a few balls, coins, etc., to demonstrate how easy it is to win. The carney then takes the mark's dough, hands him a ball, coin, or whatever and watches as the poor mark clangs the item off the target. The secret is pure physics. The carney makes the toss from a few feet away. The mark is required to toss from behind a line or railing a couple of feet further away. The extra force imparted to the objected causes it to bounce off the target. Voila. Pure profit. (It just occurred to fivedollar that he should look over his shoulder for any suspicious carnival-looking types.)

How can one invest in Tubs of Fun? Fivedollar wants to take the carney side of this transaction.

He's bananas... :)

I hope he doesn't get his money back so much.

"For once I was the sucker..." Once? I'm sure that's not his first time.
He went back to get more money...that would've been a good time to, maybe, NOT go back. And he has a kid in a stroller....and he's on the news....and the news reported it...and I'm talking about it right now... complete waste all around.

I suspect a man whose life savings amounts to $2600 has lost his life savings before.

That x box can be bought from Amazon for $165. So he used $2,600 to try to win one? He's the kind of guy who keeps Vegas slots in business. I bet he voted for Oduma.

To answer your question.
1.No.
2. No.
3. His 15 minutes of fame.