My std advice to those looking to buy is...
Define (in writing) how you intend using the boat, time distance, frequency, waters etc
List Must Haves, Wants / Nice but not all essentials and Don't Wants.
If a significant other in the picture have them do the same separately.
Then compare, combine and compromise to merge into a single list.
Research makes / models, walk docks and talk to owners, visit boat shows, etc to narrow and refine your best fit vessel.
Your objective is to buy your second boat first... avoid jumping at an early boat that catches your fancy only to find it doesn't work well for what you want / expect it to.
Make the learning & search fun vs work... make them mini vacations to boating locations similar to what you anticipate.
Lastly... consider chartering to learn first hand what works / doesn't work for you. Many say chartering is expensive but it can be enjoyable and the learnings priceless buying the wrong boat.
Good luck with your adventures
