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Oh interesting solution... Only problem with that is, you're using a lot of flecks for those new surfaces which you don't actually want/need.
Something it currently tries is to lower the sculpt detail (which means the sculpt has less flecks to convert) to see if it can fit the flecks into one painting that way. Usually succeeds, too. I've not seen the "cannot convert" message yet myself, though. Even for very high-detail sculpts--so not sure why it cannot do it sometimes.
But the conversion does take into account the detail level (fewer flecks) and looseness (fewer visual flecks even if the sculpt is high-detail). So that might be something you can try out next time and see if it works okay for you instead of needing to mess about with chopping it up.