You shouldn't have any problems sailing over anything I would think if I'm seeing just the folding prop and saildrive.
To me it looks like the separate high aspect rudders and keels that would be the most likely to get hung up under sail. Two points that will always hook up crossing a line.
Even most skeg/rudder combos have such a steep skeg that nothing will slide by.
You can raise your CB and rudder, no problems. Good Maine boat.