Welcome! You've come to the right place.
Question: What is your experience level? If you've never boated much, you might want to get a small boat or get in a club where you can get out on the water to get some experience.... AND take training.
Get yourself to a level where you understand boating and can start to think about what YOU want out of boating. With 5 years to go, you have time to own at least one, perhaps two boats or rent a lot to get that experience and then get your "loop" boat.
Also, there's tons of info out there. Jump into it. Ask questions. Visit marinas. Go to boat shows.
Stick around, we'll spend your money.