I don't plan on trailering...much. Whatever I buy will live in a marina 5 minutes from my house in Tacoma most of the year but will get trailered to the coast for a few months at a time and either live in the water there or very close to it. I'm looking for a hardcore fishing rig that will serve double duty as a cruiser/entertainer.
I sold my Shamrock Mackinaw 270 recently after 7 years. Great boat, but just needed to sleep another person or two. The Venture 29 fits the bill, and has a nice enough interior to get me the green light from the wife. Decent turn of speed and reliable drivetrain are a real plus. 18 mph is all you can really depend on in the open ocean up here anyways, at least for a boaterhome type of fishing boat. Minimum planing speed is the number that's most important to me.
Already owned an R25. Not ideal for offshore.
Seasport 27 Pilot would also fit the bill, but no outdrives for me and they are pretty tender for my taste. Outboard versions are still insanely expensive despite plummeting boat prices.
Still have my eye out of for a Tomcat, that is the smallest boat that would check the boxes. Ten years ago on this forum, someone gave me some solid advice that has served me well in boat purchases. "Don't get the biggest boat you can afford, get the smallest boat that will do all you need it to do"