Just curious, have you considered something a bit smaller as a starter boat:
Here's my pitch on small boats: they make it easy to get out on the water.
I grew up in PoCo and we owned a 19ft Larson with a 4.3L mercruiser inboard that we took out on Pitt Lake. Heavy, heavy boat - too heavy to push around the driveway by yourself and us kids were pretty useless, so everything fell on my dad's shoulders (hard working construction worker who spend all week building foundations). We towed it with a Ford Aerostar, but were likely massively overweight. Unforgiving to launch. Unforgiving at the dock. Couldn't beach it properly without scratching up the gel. It always took hours to get out to the launch. My dad always kept his cool (likely because this was childs play compared to the stress of work), but due to the amount of 'friction' to get out, we rarely used it. As a consequence of rarely using it, the boat wasn't reliable - which meant we used it even less.
Fast forward 20 years and I buy my first boat. 14ft Lifetimer centre console with a 40hp suzuki outboard. I think I paid closer to $25k (all in), which is very expensive for only 14ft - but it was built like a tank and was optionned exactly as I wanted it. Everything about that boat was about reducing 'friction':
-Light boat meant I didn't need to upgrade my vehicle, and could launch it solo (I could pickup the trailer tongue with one hand and walk the boat around).
-Kept it in the yard at the marina instead of my garage, means minimal towing
-Welded aluminum meant I didn't need to be precious about the hull, or storing it outside or beaching it - cleanup is as simple as a pressure washer
-New/fuel injected motor - started every time, less problems with ethanol (do not buy an old carb boat), highly fuel efficient and cheap to run
-Small boats allow you to learn and become 'good' at boating because everything is just more forgiving. You never see a guy in a 14ft boat swearing at his wife at the dock because he can't get it back on the trailer and is about to ram into someone. If things get squirly in a 14ft boat, you just toss someone a rope, give it a push with your foot or grab a paddle.
We had the little boat for 4 years, and typically were out on it almost every saturday or sunday between May-October. After that, I was comfortable upgrading to a 20ft centre console. But even now, I somewhat regret selling it. The new boat is great - but there is decidedly more 'friction'. Launching is more stressful, maintenance is a bit more involved, it costs significantly more to run, and if I mess something up there is more weight/money involved so mistakes are magnified. The stakes are just higher. There is nothing more fun and carefree than a small boat.
I tell everyone I know thinking about getting into boating, buy a 14-16ft car topper with a 9.9-15hp tiller motor on a small trailer for $4500 of craigslist and get out on the Pitt River or Indian Arm. Forget the hassles of insurance, a survey, etc - all required on a big boat. Take a low-stakes risk - pull the trigger and go catch some fish, explore a few beachs, have loads of fun - and if you really like it - upgrade in a few years. For many people, boating is a passing fancy, and a big old fibreglass boat can be the albatross you wear around your neck.
People get it into their minds that they need all the amenities or the family won't have fun, or be willing to go out. But the more you add, the less fun everything becomes - and its an endless treadmill of 'add-ons'. People are generally pretty rugged, and willing to go pee in the bushes if that's whats needed to go have fun out on the boat for a day. If you want your wife/family to love being out on the water - by making it easy for yourself you are making it easy for everyone to have fun. The two are linked.
