Here is an overview of some similar covers
1937 from USS Langley
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Sold at auction $22,50 plus costs, three bidders, bought by a dealer (feedback 18,300+). Note slightly different cachet and has location shown, Pearl Harbor with Clipper Stamp.
1940 USS West Virginia includes a two sheet letter.
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Cycling several months at auction opening of $60 with buy it now at $85, however, note the manuscript in the cancellation which detracts price. No location and has Clipper Stamp. Difficult to sell due to manuscript.
1940 USS Arizona
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Unsold in one auction now a buy it now at same $230.00 as auction opening. Dealer normally accepts 80% less if contacted directly or via his website. Note different cachet and long map stamp. Will sell at 80% or more when the proper buyer comes along. Long Map less common than Clipper Stamps.
1938 USS Arizona with letter and photo.
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Sold for $87.89 plus costs. Note lack of location in cancel, has Clipper Stamp.
Edited to answer posts while I was assembling this one.
Quote:
The clipper cover comes with a letter written while at sea.
Letters add interest and thus some additional value depending upon content.
Quote:
One of the V Mail letters is a poem about how he can't write about anything because it's all secret
During war it is all secret and censorship looks for such inappropriate information along with other issues. Content matters, your poem adds interest as does various drawing made by the military sender.
As to your general other covers, content can add interest but "event covers" often have no content. Also the cachet can add value, for example on USS (Meaning US Naval Ships) covers, cachets which contain one or more mermaids, mermen or images of non-white men/maids all add value and can be specifically collected for same.