Careening is no big deal if you have the right boat. I have an Islander Bahama 24 that I have careened 4 times. It has 7'8" beam and a full keel with a cutaway forefoot. The rudder is keel-hung. The keel is encapsulated lead in a thick layer of glass. The draft is 3'6". The boat sits at an absurd angle of heel when careened, but on a sloping muddy beach with good tidal range and no wake, I was able to do it without incident.
I would careen the Bayfield 25 confidently in a calm harbor. Mind the weather and tides. Fridays and Saturdays are generally bad days for this due to motor boat wakes. Make sure she lies down right side up, this can be done by making a halyard fast to a bulkhead.
I am not sure about the laws of careening, I researched them heavily, reading a lot of material and contacting a lot of government agencies, I could not find any info that was meaningful.
I would assume that it is illegal, and act accordingly. I do know for sure that the EPA would charge you fines for painting on a tidal beach.