Ideally the shaft should be tight or fairly tight in the Cutlass bearing. A bit of play up to or over 1/16" is a candidate for replacment as it will only wear away faster with the 'play' in play.
There is not that much variety in the construction of most Cutlass bearings so I would go with one that closely resembles the one in your boat now (Naval Brass vs. non-metallic).
DIY instructions for strut mounted bearings: Cutless-Bearing Replacement
Cheap webstite for buying replacement Cutlass bearings: Cutless Bearings for Sale. Buy Johnson Duramax Cutless Bearings today.
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