I'm no expert, but I don't see a distinctive "air mail" cancellation, just a regular cancellation. The postage ($0.05) is correct for the air mail rate in 1931. Tampa had airmail service on on CAM (Contract Air Mail) Route #10 beginning in 1926. Initially CAM #10 ran from Miami - Fort Myers - Tampa - Jacksonville, but in 1928 this part of the route became part of CAM #19. It is curious that it was posted from Tampa rather than from Fort Myers, since Boca Grande is closer to Fort Myers than Tampa, even considering the problem of getting around Charlotte Sound.
The three strikes of the "Via Air Mail" in magenta are postal markings. The black handstamp with "Via air mail" with the pictorial airplane is privately applied by the sender.
This cancel is not listed in the first edition of the Loso-DeWindt catalog of 20th Century fancy cancels. That listing is not complete and so does not immediately disqualify the cancel.
The rate is correct. That the 2c Washington was missed by the duplex cancel is not particularly worrying.
Still, on first look, the ink of the airplane-in-the-clouds does not match the ink of the duplex-type cancels used on the envelope. The stamps are only lightly touched by the airplane-in-the-clouds, barely tying stamps to the cover, so very tentatively struck. These factors make this very unlike the fancies of the period.
So I don't believe this to be a cancel, even unofficial; the great majority of the fancies of this period were not authorized by PO headquarters but were allowed by local postmasters. The airplane-in-the-clouds could be a fake added later to a plain airmail cover.
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