The bicycle strongly resembles the ancient hand-me-down Elgin upon which I learned to ride. The heavy frame featured a second upper bar exactly as shown here.

From recent research, I believe mine was an Elgin Four Star model. I can't see the characteristic painted stars on the fenders of the bike in this photo, but everything else matches my memory.

This was a massive bicycle, really too large and heavy for a young rider. Even with the seat all the way down, I could barely reach the ground. I had to walk it up most hills, as it was a single speed. The very large balloon tires gave it a very nice ride. Like a lot of long-gone things, I wish I had it today!

That sure is a '40, for all the reasons you state. Another spotting feature is the wing window. 1939s didn't have them.

The wheel bolt pattern on the model A was the same as cars up until '48, and even later on five-lug pickups. This cars' change was probably done to take advantage of the better tires available by then.

Black sedan is a 1940 Ford Deluxe Tudor (you can see the Deluxe script on the side of the hood )with an accessory spotlight and accessory bumper guards on the end of the front bumper.

At first I was going to say '39 or '40, but the steering wheel is a '40, '39 would have a banjo wheel.

I remember getting a bike plate in Florida even in the 60's. We filled out a form and paid a few dollars, and got them at my elementary school. We looked forward to it since we thought they were cool to have on our bikes.

I looked at Model A Fords on Google Images and couldn't find any with the 'large' wheel hubs the car here has; it had me wondering if it really was a Model A, but the tail light and bumpers say it was. Apparently later wheels (Model B?) could be used.

Harold probably got much of his sign's cost paid for by 7-Up for advertising rights.

Howard must have been pretty prosperous to afford custom neon on his signage. Wonder what image was on top of the sign? Had to be a chicken....right?

All bicycles had to have police issued license plate in the 40's?

According to https://volusiahistory.wordpress.com/2014/02/15/early-daytonas-forgotten... 2nd Ave is now known as Dr. Mary Mcleod Bethune Blvd.

https://goo.gl/maps/UuGw392TpYw

Delivery available today! Harold's is a Chicago institution!

If you are good today, we will let you deliver the phone order on the bicycle.
If you are not good, we will make you drive the (between 12 and 16 years old-depending on how close it was to a 1927 or 1931 production) Model A Ford. That is, if we have any ration coupons to put gas in it.