A few years ago I started with a 27ft single engine boat. The idea was similar to yours, a weekend retreat. After a year, we decided that we loved it, and then moved to a 38ft boat with twin engines to have more comfort for sleeping, etc.
We love it. You can learn to operate the boat in time. Just go slow. I still do!
We come up every Thursday or Friday and spend the whole weekend, even if we never leave the dock. It's like having a summer camp. Sometimes we go out on other boats, sometimes we take people out with us. Of course having a slip at a nice place helps a lot!
Trailering a boat gives you access to many other boating destinations. But my boats were to large to be trailered. Not a problem for us, as we love the lake.
My thought is that with a rental or day boat you miss more than half of the experience, but it depends on what you are looking for.
Good luck with your choice.
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