Have decided I’m pretty set on an outboard runabout. Really liking the 20’ and 23’ Rossiters but they are spendy. Does everyone think a deep V outboard would be a good platform to start on? Any other options in this vein that would be better/worse? Thanks all.
I have to disagree with the runabout recommendations...
Ask yourself why a trawlers appeals to you? And also what part of that is satisfied by a runabout?
If the simplicity of an outboard is attractive there are trailerable pocket trawlers. When I think of a trawler... even a micro one like a C Dory it's the ability to travel... medium to long distance and to stay over nights aboard. A CDory, Roxborough, CutWater, Ranger tug and others allow cruising to a distant location and staying over night(s). A runabout is a day boat that provides none of the trawler characteristics.
To me runabouts as a prelim to trawlers would be similar to trying day hikes to see if you would like a self container RV, motorhome or 5th wheel. There are more differences than similarities.
We started boating with a 24 ft i/O Cruiser and it convinced us we liked cruising but needed a different boat to fully enjoy cruising. A runabout would never have exposed us to the appealing aspects of cruising.
Just something to think about... define carefully how you want to use the boat, musts, wants and don't wants... all in writing. Then go walk docks to find others doing what you want to do and ask what they like about their boats that fits with their cruising style.
Thinking ahead let's you buy your second boat up front and avoid a costly swap to get what you really needed/wanted.
Consider renting / chartering as a way to explore different styles and to evaluate how well each satisfies your desires.