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Level cap penalty
All skills have a training cap of 100 points. Horatio's bonus cannot be used to exceed that limit, so collect it before you reach the cap. If you get his boost when you are already past 100 strength he will reduce your strength to 100!

Horatio is one of many who got thrown into the Colony for a minor crime (in his case, he accidentally killed a man) and is now serving a life sentence for it. He says he can teach you how to be strong like him if you can give him a good reason why (the available choices aren't satisfactory).

To get a good reason, go to the pub and ask Jeremiah about the Rice Lord. Go back to Horatio and he will now be satisfied with your answer, and awards you with +5 strength for free.