As for the paint or no paint issue: Do you think that the paint is a good "sealing" material? Generally the concern would be that the coolant, in time, may lift the paint to block contact surface, this also aided by corrosion effects, then allowing the coolant to migrate between and to the exterior.

So generally, "no' one should not allow the paint to remain.

As for the gaskets: Without a heat-cycle event, as long as on disassembly the surface material or coating does not adhere to the head or block, or become damaged, then yes, even though one would prefer not to practice this, you should be O.K..
Another possibility if your uncomfortable with the idea of possible gasket damage or of a "re-crush" scenario would be to just reduce the torquing spec. "some", say 20 ft. lbs., follow through with your oil testing procedure, and if the heads don't need to come back off then just follow though with the final pull or a proper "re-torquing" to the full ft.lbs. spec..; but then if they do, 'maybe' the lesser torque number might help in not scrubbing the gasket surface so hard and better your chances for reuse.
Scott.