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I have actually been to the Crooked River Roundup...and many other fairs, and racing on even consecutive days is not completely unheard of. Keep in mind they are running sprints on a short track, and these fair jockeys out west take it easy on the turns, so you are full out for 2-3 furlongs at best.
Also note that as these fairs scramble to fill fields, you end up with many entrants racing out of conditions, like an open race with maidens and NW2L types. Allowance races open to the world, etc. Many uncompetitive entrants, leading to less than taxing runs for the winners. I would say if the horse did not race well first time out I would not look for much improvement a day later.
Steelwood, of whom I am sure more than a few folks here remember from back in the day, won consecutive races at Keystone and Pocono Downs, when the racing secretary at the latter apparently refused to allow him to scratch.
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