Grady 23 - in some states trailering anything wider than 8ft 6in. applies restrictions to ban such trailering altogether on certain days of the week or holidays, or hours of a day unlike if it was maxed at 8ft 6in. Weather or not a law is enforced is for each of us to decide what-if when making such an investment with a no-return policy.
The grady product like takes the 20 ft walkaround and extends its length to 22, 24, and even 26 ft (Islander) all at similar beam all trailerable (legally). The so called wide beam models begin at the Gulfstream where it is basically a shortened Sailfish. Unlike the Sailfish, the Gulf can do fine on one motor most left the factory as singles, same for Islander and shorter narrower beam models.
Gulf and Sailfish cockpits/bridges are similar, big big difference in cabin.
Twin motor equipped boats as options over singles are much more expensive and have higher fuel and double maintenace costs, twice as many things to go broke, and double the replacements costs when the time comes for new power.
Just remember, there is always a bigger boat to buy.