We had this discussion this morning:
I started my Grady journey with the 275 Tournament 2010 model with twin 150's purchased in 2012. So I am familiar with the boat, 8.6 beam and the handling characteristics. I used her primarily up and down the Chesapeake bay. Often I say beam and weight is everything but I am going to revise that. I now have a 33 Canyon that is extremely comfortable due to beam and weight. But in between the 275 and 336 I owned a 228 center console Edgewater. The beam was also 8.6 on a 22-23 foot hull with a single 250hp. The weight difference was 4900lbs vs 3000lbs. You could imagine my trepidation to "downsize". I made the decision to downsize because at the time we were considering a larger cabin boat but I always wanted a CC for fishing. The 228CC overall with one engine centerline performed a ton better than the 275 stretched out with the same beam. On the 275 if someone moved to the side I was ALWAYS correcting by moving in the opposite direction. No use correcting with tabs as they were to slow. I would say she was riding on her rails if people moved to either side. That was not an issue in the 228 with same beam and engine located on the centerline and 1900lbs lighter. The 275 was a much wetter ride compared to the 228. She was notorious for taking spray in the tight chop of the Chesapeake bay. All this said, the 275 with a family of 3 boys 6,9,12 was the best decision for spending time together and I fished a ton with her. I was so worried to downsize thinking we would not go as far to destination weekends and that was simply not the case. The 8.6 beam is just suited much better for a smaller hull than the 275.
In short I think you will notice a huge difference in picking up that extra beam and the engine package is such a great motor. And you are buying a boat that many people want so your resale will be excellent. The beauty of the 275 was selling her 5 years later for exactly what I paid -2K. By the way we never got the larger cabin boat, held the 228 for 4 seasons until upgrading to the 336 Canyon. I look forward to hearing the differences of the two boats after you put a few hours on her. Good Luck