I see that this old thread is back in play again, so I will add a few comments that I hope will be helpful.
On my Hunter 26.5, I have the same port tack drag issue, but it's not bad with the 20" shaft 9.8hp I have now. The big problem that I have is the lower unit coming completely out of the water in heavy seas or when making a hard right turn. A 25" would help with that, but at the expense of adding extra stress to the transom. The bracket itself seems fine, but the transom already flexes more than I like. I would add a couple square feet of 1/4" G10 before going with a longer shaft on that boat.
One strange thing about the way that mine is set up is the prop. I have a 3 blade with a steep pitch. I get a lot of slip when I give it the gas. Performance would probably be better with a 4 blade, low pitch, high torque prop, but I don't want to add the extra stress to the transom at this time, so I just leave it as-is for now.
On a recent 25 mile trip with a 2.5 knot current & 10 knot breeze both dead on the nose, I was able to average about 5mpg just motoring, while making just over 3 knots average headway over land. A buddy in a Cherubini 27, with a similar motor, burned about twice as much gas on the same trip, the same day. That boat is a couple thousand pounds heavier & I think that he lays on the throttle a little harder than I do. I was below 3/4 throttle & felt like I was near hull speed.
A longer shaft will cause more drag & likely increase your fuel consumption.