When the going gets rough a shorter shaft will let you down.....not a peaceful thought. Spring for the long shaft. I had a long shaft on my old 240 and never had any issues. There's been a lot of discussion about what hp to go with and my experience with that boat was that a heavy 9 or 10hp 4stroke will cause a serious list to starboard. I'd say 8hp max and 6hp min. After all, it's not a powerboat.
For just a few bucks more I'd defiantly make sure you get one with an alternator too. An effort to request a prop sized for lower speeds and high thrust will add to your joy and will be better matched for a sailboat vs a bass boat type app.
Good luck, Mike