Wifey B: Go to a golf forum and ask if you should take up tennis or golf and see what answers you get.
The last few weeks we've been limited to weekends and oh my thank god we had speed.
I'd suggest talking to some others, for instance maybe find a Sea Ray group or something and talk. Compare notes. There's a reason most weekend boaters, especially those with kids, don't have trawlers. They're still living life in a way that time is even a more precious resource than money. Then when they retire, it reverses.
How old are you? Who will be with you? Look at what others similar to you have. The "starter trawler" arose in this discussion. I'd suggest think "starter boat" and it's likely smaller and faster. You don't need the same space and amenities for 2-3 day cruises that you do for 6 month cruises. Don't need to carry as much with you. Can live a little more cramped because when you reach the destination it's going to be "run wild" time.
You can get like a 30' Sundancer for $50k and people will tell you gas engines and stern drives won't last as long, but how many hours a year will you actually use it and it can be kept perfect in dry storage. Or older Sedan Bridges for half that or 34-35' for double that and then into diesel inboards. A ton of Bayliners in your area since they were built nearby.
Go to Yacht World and play around. I just found a 30' Apreamare for $75k. Twin DD's. Detroit Diesels guys.....there's more than one type DD. Cruise at 23 knots. Some Nordic Tugs cruise 7-12 knots with WOT of 15-17. Bayliner 3288's, a great place to start.
Don't think type boat or label, but think of you and your use and your experience. This isn't your retirement boat to cruise the world. This is your boat to get out on the water and enjoy and learn and then dream of the retirement boat but know what you want by the time you get there.