Besides any jewelry he might be wearing, he might have a watch. Even an el cheapo digital one is going to raise eyebrows (I'd go person to person sale rather than the pawn shop with that).
Yah it would rais eybrows, but I don't think he could sell it very easily, it's too different and odd. There are people who would buy it, and for a sizable chunck of money, but not most people he could find on the street, or even in a clock maker's shop. Also he doesn't need to raise a lot of money, just enough to get to Washington with a bit to spare.
He could pass some of his UT coins by putting them into a stamp vending machine and then selling/exchanging the stamps (at a slight loss) to someone (after a semi-sob story;-).
Not a slight loss, a HUGE loss.
Any one of his coins is a nearly unique coins with obvious signs of wear on them, but in reasonably good shape. With no providence he could get really high but he could probably get a dollar or two per coin, with the pennies probably being the most valuable.
Also, I doubt the coins he has would work for any vending machines in 1936 - their weight would be wrong and I believe that was the first test for fake coins that was added to vending machines.
The big problem with that one is his money is basically already a big federal crime if he's caught with it (again counterfeiting...even possession of money that presents itself as legal tender is a crime whether you try to pass it or not).
That's more of an issue with the bills than coins as long as he doesn't pass them around except as odd collector's items he found.
He has the fastest car on the road as well (in 1936 the Rolls Royce Phantom III clocks a 0-60 time at 16.5 seconds...his Corvette should be around 6.6 secs). He could offer rides for a nickel or find a race.
Good point.
I'd start sniffing around Detroit
Henry Ford might be there, or he might be in Washington DC(He was involved in politics and by this point was not involved in the day-to-day operation of his company), or in Dearborn Michigan (Ford had a large factory complex there), or any number of locations including various vacation spots around the world. But even if you know what city to look for him in, that still doesn't tell you where to actually find him.