If you have a spot on the lake for the boat all summer then you don't necessarily need to tow--it depends on what you plan to do for winter storage. A trailer could add $2K to the price and that money might be better spent on the boat itself.
I love all boats, there's no wrong hull style, they all have pluses and minuses. That said, I vote +1 for a pontoon. If your budget allows, by all means go for the tri-toon! But if cost is an object, a 20' gently used two-toon with min. 75 hp motor would be a good first boat choice, IMHO. Docking will require some learning but they are stable & tough & easy to maintain.
Most marinas do post the prices of their used inventory. You can rent a boat for a few hours to try different styles, since you are new to boating it would be a worthwhile investment to see what you and the family are comfortable with before buying. You could also attend marina in-water demo days, but they are mostly held in spring.
Happy shopping!
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