Yeah this is the first really tricky election I think because while board 8s values are with the Federalists generally, this ain't really the party of Adams at this point.
It was well-known for instance that the famous Burr maneuver would have probably been attempted by Hamilton to make Pinckney president had the Federalists won last time - Adams is well-justified in telling these people to take a hike.
And so on the merits, Jefferson and Pinckney aren't really so different - the main differences being tax policy, defense policy and relationship with France and England.