The following are some non-binding "rules" that should ensure a good time is had by all.
How to Make a Good Mystery Picture
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Objects in the mystery photo should be able to be observed from a publicly accessible place.
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The mystery photo should be taken in San Jose. That is to say that it is within city limits or on the outskirts of town.
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The objects should not be something that is likely to change significantly so as to be deemed unrecognizable in between the time that you take the picture and a guess is made.
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Something about the object should be unique or unusual, whether it be the object itself or the object's relationship to its location. (Ex: A picture of a "No Parking" sign is a bad idea, unless it's found sticking out of a tree.)
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The object should be guessable without hints, or an initial hint should frame it in this way.
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Once you're ready to post your mystery photo, think of a list of progressively more revealing hints to provide in case nobody guesses correctly. The hints shouldn't stand alone, and should only be used after it's clear that guessers really don't have a clue.
Breaking the Rules
Photos that relate strongly to San Jose but are not in San Jose (say, a shot of astronauts doing a spacewalk wherein one is from San Jose) may be pretty good. If it's not obvious, you should probably make it clear in an initial comment. Something generic or unguessable might be guessable by an event or circumstance that makes it memorable. In general the above rules are pretty good guides, but don't feel utterly bound to them if you have a good San Jose-specific and guessable image to use.
How to Guess
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The best guess will be in the form of a picture revealing the larger contextual location of the object.
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The second best guess provides a location of the object precise enough that others could also find it.
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Ask for hints before asking questions
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After the Mystery Photo poster has run out of hints, ask questions phrased in a yes/no format, such as "is it at San Jose State?", or "is it edible?".
When Does a Photo Go to the Unsolved Box?
(after X incorrect guesses...? or after Y days of inactivity...?)
- Inactivity seems like a better choice than number of guesses. There could be many guesses because the picture is not obvious, is not something people have come across, or because a lot of people are interested in that particular picture. Inactivity indicates lack of interest (or possibly that no one watching the picture anyway.)