[playinghooky]

I have a 20 foot 4Winns and feel that it is adequate for what we use it for on the lake. Most of the time a 20 footer is fine. But there are many times a bigger boat would be much more comfortable. I would not want to go any less than 20 feet though. Many afternoons the wind kicks up and you wouldn't want to be out there even with a 23 footer. With a smaller boat you have to be more careful of the times you go out and stay in if it's too rough. Keep an eye on the weather for any approching storms (but you need to do this even with a bigger boat). If you plan on trailering it, a 20 footer is much more practical and easier to trailer. Other advantages of a 20 footer is you would use less gas, it's much less expensive to buy, easier to dock and easier and cheaper to store. If money is not a consideration then go with a bigger boat.
Yes a 23 footer would give you more comfort on a bad day but a 20 footer is adequate most of the time. I would recommend you look at the 4Winns at Melvin Village Marina. Since you will be in Moultonboro they are very close by. If you ever need service you don't want to go hauling the boat all the way to Winnisquam. Melvin Village Marina gives excellent service and fair prices. Many people will bad mouth them because they will not do any service on a boat unless you bought it from them. But when you do buy a boat from them, their service is outstanding. Service can be very important. My starter went out and other marinas said to bring it in and put it in line for a 3 or 4 day turn around. I brought it to Melvin Village at 9:00 in the morning on a Saturday and it was fixed by 1:00.