It really depends on your needs. We've had 3 places on NewFound. First was a shared beach which was a bit of walk. We had an 18' I/O back then, but a pontoon might have been better since we would spend 1/2 the day on the boat. We were in the boat a lot to have our own "space".
At our second place we were on the water and had the dock below along with the Tige. Having breakfast on the dock was like being in a Pontoon. Maybe better, because no waves, bathroom in reach and great if you forgot to pack something
So the only time we went out was for "sport". Pontoons are probably the least good at sport.
The Tige was horrible on chop though because the bottom was so flat.
As far as maintenance. They are all pretty much the same. They all need to be winterized, protected in winter, oil changed and cleaned. Pontoon looks easier to clean the bottom, but that's about it. Well, you have no windshield to keep clean.
My Tige was pretty heavy for towing. 4500 lbs for 20 ft boat. Pontoons are lighter but catch a lot of air.
Another pet peeve of mine is, I like a real windshield. I like going out when it's glass early to ski. But it can be pretty cool. I'd freeze my ass off in a Pontoon boat.
Also covering the boat. I always used a full mooring cover and always will (unless I have a boathouse or covered lift). Putting the cover on our Tige probably couldn't have been easier. Covering Pontoons looks like a PITA. I watch neighbor do it all the time. And I've done their boat a couple times. I could borrow it any time. And theirs is on a lift and it's still painful to watch.
There are tons of Condo's, Day Trippers, Shared beaches that a Pontoon is better for being on for the day and partly why they are so popular.
If I was on Winni, I think I'd want a Deep V 26+ footer. Maybe with a mini head. But again, locations vary a lot. You might live/stay in a calmer bay and never cross the broads, ever. Or you might live on an island.
Currently this is my "low maintenance" stop gap.
Water was pristine here, sandy bottom and perfect gradual depth. There wasn't many better places to be.
It even had comfy seats suspended over the water. It felt more in the water than the boat did. And literally no maintenance and no gas. Why go putt putt in a Pontoon?
Even the ducks know a good thing
