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Does anyone other than myself wonder about stamps that cost at least several hundred dollars and yet don't have a certificate?
Not necessarily. It depends on what the item is. For certain stamps, a cert may be necessary for authentication purposes, whereas for others it may be for condition... or both.
Also, it depends on the market value compared to catalog value. Some stamps are prohibitively expensive to certify compared to what they garner on the market.
For example, let's say you have a stamp that catalogs $5,000. If it is a sound VF copy that you expect could bring $2,500, then it's likely worth expertizing. However, take the same stamp with a fault or two, which might only bring $1,000, and it becomes a bit more iffy of a proposition from a return-on-investment perspective. Why? Because the expertization cost will be the same 5% of Scott regardless of condition.
$250 (plus registered or express mail both ways) is a bit over 10% of the expected return on the first stamp, but over 25% of the second.
Experization is not always cost effective. As a buyer, it then becomes a question of whether you are knowledgeable enough and comfortable in that particular area to risk buying without a cert.
In my case, certain revenues I will buy without certs, as I feel I know enough of the diagnostics, but others (some of the part perfs, 2nd issue RB roulettes), I still insist upon a cert or extension.