Dave's question on long term effects of oversizing the outboard was partially answered, same thread above. My 2000-26X with Suzuki DF60 is now in its fifth season.
Frank C wrote: . . . When I asked my Mac dealer to upsize to a (Suzuki) 60 hp, he told me the same thing ... that the transom is amply designed, but that the manufacturer might not warrant it. He discussed it with Roger Macgregor, and they refused to warrant my hull with a 60hp. However, they did express the same opinion, that the transom is not at risk. They were nervous about the hull to ballast tank seams, should I choose to go pounding across choppy waters.
TRANSOM
Repeating comments from above, the transom is well designed, perhaps "over-designed." Keep in mind that the X was the first-ever "heavy outboarded sailboat" in the industry. Roger wasn't about to mess up on that. We learned that the factory had tested the transom with a Merc Bigfoot 50 . . . by trying to tow a pier!

. . . with no adverse effect.
My Mac dealer insisted on stabilizing the transom, spanning it inside with a heavy aluminum channel, sized ~like a 2x3 stud. This reinforcing channel carries the lower motor bolts and the rudder mounting bolts. Scattered owners had installed the Suzuki 70 with no reinforcement, before I chose Suzuki's de-tuned DF60 version. Both models weigh 335#. (It seemed to me that Mark's problem on his 115hp was installation-related, not inate to the transom).
BALANCE
One of the '99 manufacturing changes was enlarging the forward bias of the ballast. Also, adding the forward vent permits more positive filling of the tank. I concentrate my heavier gear (tools & water) at the center sole and fwd dinette, and I have anchor and chain on the bow (~50#). I keep only lighter stuff (PFDs, etc) on the aft berth. My boat's heavier motor does not noticeably affect attitude or sailing performance. The boat floats perfectly level to the bootstripe w/ 3 aboard.
I can easily imagine somebody with a light 2-stroke 50hp having a greater balance problem than me. If you store lots of gear under the cockpit and if your crew size is 4 or 5, you'll quickly surpass the aft bias of my 60hp outboard.
MY EXPERIENCE
My motoring performance was 24 mph at 5000 rpms in light ripple when new (GPS). As the boat aged, WOT has dropped to 20 or 21 mph. I could probably add 2 mph by re-pitching, since max rpms should be 5600. However, I never run the boat above cruising speed, about 16 mph @ 3,800-4,000, so have not bothered. My 3 personal best days under sail were close reaching at 8+ mph and kissing 9 mph (7+ knots) in 20 knot winds, by GPS. This required lots of practice and additional trimming and sail controls, but nothing special regarding the motor. The transom exhibits no signs of abnormal stress.
RISKS
As mentioned in the quote, ballast tank is seamed to the hull, and the factory expressed the opinion that this was at risk by overpowering. Using a more powerful motor to push the boat through heavy chop could quite obviously stress those seams, especially with ballast full. As described, I rarely run WOT, and scrupulously avoid high speeds in heavy chop . . . besides being uncomfortable, I hate to punish my boat that way. I rarely motor with ballast full, never motor at speed with ballast. Only one time did I have 5 aboard, and rarely have more than 3.
BEYOND
I think Billy chose to go with his 140 after hearing my experience was so benign. I also referred him to two others with Suzuki 70s. I would not hesitate to follow his and Mark's path with the next larger Suzuki at 400+ pounds. Billy's 140hp is only another 75# more than my 60hp, and I believe the the fuel economy difference is trivial.