@mcipinkie good advice has been giving. Why not try looking at used boats of different size and power that you can actually get in and drive and see where your comfort level and needs are. You will be amazed at the difference and skill level it takes with different boats. Good luck on your journey.

23 hours ago, GreenvilleSC_fishing said:

I have zero experience with boats and have only ever been a passenger. There would definitely be a learning curve. Rather than dollar considerations, I am curious how difficult this is for someone who is technically minded but does not have previous experience. I’m curious if newbies harm boats and motors from lack of maintenance experience or if the list is fairly manageable (things like winterizing motor).

 

Like I posted earlier, this was my first concern when I read 21' 250 HP and first boat.  It's not fishing or even driving the boat that is the problem it is all the other things.  Backing the boat into the garage, towing, launching, docking your boat, loading your boat in a breeze or with current- these are all potential areas to have little accidents.  And all repairs on a glass boat are expensive.  As a boater/fisherman, there are so many opportunities to make a little mistake that ends up costly.  These are just things you learn over time.  As someone who has had a boat for over 20 years, it wasn't until I had a couple boats and made  several mistakes before I really started feeling confident in my ability to own a new boat and not beat it up.  Maybe you're more careful or take care of your things better than me but I know I would have beat the hell out of a big bassboat when I was an unexperienced boater in my 30s.  Thankfully, I had a used tin boat for a while before getting a new fiberglass boat and things have gone relatively smooth.  

 

In terms of maintenance, you can rely on your marine shop or just follow the owners manual.  There are Youtube videos for everything.  Good luck.  

"Shorter" boats and fishing with more than just you are not ideal. With two young sons on lakes like Hartwell and Keowee, I would definitely be looking at larger boats. It will be more expensive in every way, but it'll be a much nicer and safer user experience. As mentioned, if you have the budget to buy, maintain, operate and store it, it'd be my suggestion to go bigger.