Mantle, you asked Dave, but many of us live on the water on the south shore.
Your best bet is to go out Tuesday morning at the peak tide and look at houses you might consider. Don't buy the ones that are flooded. But you probably aren't game for that approach. You might consider driving around a few days after and see who's having a "yard sale" of soggy carpet.
Anything built from the 70s on, people were figuring it out then and tended to build a little higher. My house was built in 72 and doesn't flood. It's up a foot or two from most of the neighbors. Older houses you have to watch. Look for water lines i.e. bathtub rings, especially in unfinished areas like garages. Look for boilers on cinder blocks. Look for fresh paint jobs.
Before I bought my house, I looked at a picture of the peak of the 92 storm, and saw where the water came on a dock ladder at a club I belong to. I measured from there to the water surface, then drove right to the house I was looking at and measured up from the water. Then eyeballed where that would come to. All sellers will say all houses don't flood. Mine turned out to be truthful.
Maintenance? No extra on the house. But don't buy anything for the yard made of steel. Powder coating looks nice the day you buy it but not soon after. Aluminum is your friend. So's wood.
Bulkhead is impossible to say. See if you can get someone knowledgeable to inspect it, like a dockbuilder but they tend to be busy guys. A regular house inspector may or may not know anything. Usually someone who is selling has not spent tens of thousands to get it redone so he can move and not get all his money back. Figure you may have to eat that job once, but if you do it with the right material, only once.
Your insurance costs may be triple what they are elsewhere. You probably need a specialty "non accepted" carrier for homeowners, the regular guys won't touch you unless you are very far in from the Bay. Plus flood. I understand flood could be higher now. I got mine before the flood maps changed so my rate is somewhat locked in. You want to research this carefully before making any bid on a house; I did and almost walked away.
Against this, free dockage for boats and the ability to see how they are doing 24/7 by looking out the window. No marina hassles. Many great quality of life enhancements that I would not trade.
