Generally, in my opinion, the biggest problem in boating is "you." Knowing why you boat, knowing how much money you're willing to spend, what you're willing to learn and do, what you intend to put up with, etc.
Owning a boat requirers effort and money; how much of either is up to you. Being on the water generally means we're trying to enjoy ourselves and spend time with friends and family, so we have to put up with other operators and such to do that. Gettin' wound up with everyone else ruins your time with what you want to do and who you want to do it with.
What you want, and what you're willing to do and how much you can spend on it are probably the biggest problems with boating.
I bought a tinny with a 9.5 HP outboard. It was small, but it was big enough to enjoy vacations with 2 fat adults and 2 pre-teenage boys. I paid $600. The motor had just been reconditioned with a tune up, impeller, etc. I rebuilt the trailer and painted it with rustoleum for another 100 bucks. A traveling cover another 60 bucks.
Since owning it I put another 100 bucks in the motor and another 100 bucks for trailer tires. Annual maintenance for grease, plugs and winterizing too small to itemize. We never used more than 3-4 gallons of gas for an outing, and no more than 20 gallons on a week-long vacation. The Homeowners insurance covered liability, so no cost there.
Those are the total costs since we bought the rig in 1986.
How can you put a price on the memories we gained in the past 37 years. We only spent pocket change, yet our return was simply priceless. One of the best investments I ever made.
If you NEED an I/O, and you NEED 50 mph, and you NEED to take a dozen people with you, then you NEED to spend big bucks, now and again every year. If you want a family value, it can be done for literally pennies.