Tire Pressures

Do you have the inner tubes with metal stems? If so, did you install them yourself? Did you use rubber glue to seal the stems? Or did you buy the inner tubes with the metal stems already installed? I have found that the tubes with metal stems tend to lose air more rapidly than those with the incorrect (but more practical) rubber stems.
If, however, you have rubber stems, did you insert them into the wheel yourself? If so, you may have slightly pinched the inner tube so that it has a slow leak. Also, try replacing all the air valves inside the rubber stems. They may be defective or not tightened properly to seal. They will leak even past the rubber caps. The valves are cheap enough that it will be worth your while to simply replace them all.
Depending upon where and when you bought the inner tubes, a couple years ago there were some poor quality tubes being sold that leak air through the rubber. This became such a well-known problem in the Model A community that at least one national vendor made mention in his catalog that his tubes were of better quality and wouldn't leak through the sidewalls like the inferior ones were doing. Maybe you got stuck with the inferior tubes that will leak forever?
Are there any patches on the inner tubes? If so, they may be leaking or have deteriorated. Any kind of rough surface or small projecting rusticle could have worn a pin hole in your inner tube that allows air to slowly escape.
Finally, do weather temperatures fluctuate wildly and rapidly where you live in Florida? Tires usually lose air during cold winter months and must be aired up again when the weather turns nice. If your weather changes rapidly, your inner tubes may be losing air in the cold temperatures. Is this a new thing with your tires or did the situation only develop over the winter?
Marshall
 
I use a little spit to form a bubble over the end of the stems to test for a leaky valve. I started doing this as a teenager. It was probably the result of one valve leaking. I carry new stems and a tool to change them in the car.

I would advise to replace all the tubes and use some talcum powder from Aircraft Spruce to keep the tubes from chaffing against the tires. https://www.aircraftspruce.com/catalog/lgpages/tiretalc.php

Another option is to put some Slime (the green stuff) in the tubes, but it makes a mess and is not a cure but a band aid.
 
Speaking of stems, is there a reason why the are so long? They would be easier to fill if not so long.
I read somewhere that the early iterations of the Schrader valve internals were much longer and necessitated the long stems. And repros have kept that length for authenticity.
 
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