
I had the same problem, until I realized that the "so" goes with "said".
"to say so" = to assert
To fix this sentence, I would either put a comma...
Tom said so, many times.
or change the word order
Many times Tom said so.
It's surprising even to me how often meaning in English depends on intonation. This point should be remembered by all in discussions of "natural sounding sentences". What is natural and comprehensible in spoken English, may be ambiguous in writing where we don't have the benefit of intonation. I just noticed this the other day while translating some English sentences with audio.
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