(loop for i from 0 to 100 with c = 0 finally (return c) do
(loop for d across (format nil "~A" i) do (when (char= d #\5) (incf c))))
How about:
(loop for i from 0 to 100 sum (count #\5 (princ-to-string i)))
(count #\5 (format nil "~{~A~}" (loop for i to 100 collect i)))
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