Might be cheaper to have another boat on the other side of the bridge.If you had a deck stepped mast, you could at least get an additional six feet of bridge clearance by replacing the compression post with an oversized tube. Then the mast could be retracted into the tube.
The mechanics of it might be complicated and prohibitively expensive , and the location of the boom gooseneck might be a problem when all of that gets to deck level.... and the list of disadvantages continues.