Beautiful site. I visited Maine and was at York Harbor and Bar Harbor too.
I see a problem with the roofing tin. It should over hang the drip board by around 1 1/2 inches. You can do a quick fix tho with a 6" strip of flashing. You will have to remove nails/screws at roof edge tho to slip the flashing under the roof tin. Then nail/screw/caulk back thru original holes. If you do not, you will be faced with rot sooner than you think. A stitch in time saves nine?