I agree with Archaea's post and would add that enough base miles is also important for strengthening other foot and ankle structures, including plantar fascia, long plantar ligaments and the bones which may be susceptible to stress fractures.
If he's done it before, he can likely do it again. But risk of injury is going to go way up as compared to someone who has built up to it over a 2-4 month period.
This is all assuming that the 14.5 miler was the longest training run this season. If he's already done an 18 miler, then that would change things quite a bit.
The blister is also a cause for concern. If its fully healed then it should be no prob. If its still there, expect it to fester before too long on saturday.
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