I've always wanted to do a waterfront like that. It's the logistics of how to raise the buildings (and the rest of the board) above water level that gets me. I want my buildings to be individually based and usable for a variety of games...

Mike Demana
One thing to consider, might be PDF buildings, traditionally made with card stock, but I print them on regular paper, which I glue to 2mm thick chipboard. They require a little out-of-the-box thinking to build but they are
not difficult to assemble. Best thing about my chipboard buildings?
No painting required, other than blackening the cut edges. For edging chipboard buildings, a black, brush tipped, acrylic paint pen is your best friend.
I use MDF cut to size and shape, to base my buildings, when/if necessary: round
cardboard tube Tower;
Marx toy wooden fort, converted to fantasy 28mm game terrain;
chipboard Siege Tower project. Cheers!