Question #3 was answered today.
No big surprise on the answer (scroll down a few posts). But, we have question #4 now:
Oddly, I think I saw something on the history channel on this but I completely forgot what it is.
The answer.
Thank you to site member Danny for finding the answer. To get it, you go to the You Can’t Win page (under On-Air) and after a few seconds a big red HINT button appears just under the top image.
Hopefully the image isn’t too large.

“Florence Henderson and Frank Vincent both at at Anthony’s Coal Fired Pizza”.
Edit: The image is a little large but you can see the important part.
Again, thank you Danny!
Question #2 was answered (finally)
I missed the name but today’s caller got question #2 correct:
So now we have question #3.
Question #1 has been answered!
Already? Here’s the answer and question #2:
You Can’t Win has been won!!
Today’s caller, Jeff from Port St Lucie won You Can’t Win. At first they called him wrong until he explained his answer (interchanges = entrance / exit set)
Here are the six questions:
Question #5 has (finally) been answered!
What do Jefferson and Nixon have in common?
They both have the same middle name: Millhouse.
Jefferson Millhouse D’Arcy (from the TV show Married With Children) and Richard Millhouse Nixon.
This also gives us the finale question #6:
There are 188 of these in Florida, what is it?
Question #4 was answered today!
Today’s caller, the “not so lovely” Linsey had the correct answer today:
Who mysteriously and eerily predicted in September 2006 that the P&YR show would be heard in Key West.
Brad Neltzer – in the “Book of Feet“
And this gives us question #5:
Question #5: What do Jefferson and Nixon have in common?
I have a feeling that we’re going to have to think outside the box again – and maybe not the actual people.
Question #3 has been answered (finally)!
Today’s caller, Mike, got question #3 correct.
Which also gave us question #4:
Who mysteriously and eerily predicted in 2006 that the P&YR show would be heard in Key West.