If you have bought bigger boats, which I assume are the too big to be trailerable variety, you can apply some of the same buying principles i.e. don't buy new & don't buy from a broker.
Set out your wants with the must haves & nice to haves. Do the research on builders. Don't be buying a Bayliner or a Sea Ray of the highway. No need to buy a Nordhaven or Outer Reef either.
The are a few decent 5er builders left out there. No harm in buying a used one if it has been taken care of. Like boats a bundle can be saved buying used. Some of that can be used for updating.