I see by you picture you are not new at riding, But some thoughts on seats. I do not have a Day tripper, I have a Mustang two peace seat. Mostly wanted it for the passenger seat. While the passenger seat is two inches wider and thicker than stock, that is want we wanted. As the wife would want to stop every 40 or 50 miles to rest. The after market seats have a better padding also slightly firmer to take up the weight without just collapsing to nothing. So the bigger look is just taken in stride. Floor boards helped for the wife also.
I was not unhappy with the stock rider seat although the Mustang seat is some better. It's better firmer padding and moving me forward a little helps. Posture is a big factor for riders on a cruiser. We lean forward slightly with arms apart in that cool Easy Rider, Bronson, Wild Hogs, look. The seat didn't do much for the cramps in my shoulders. I added an inch and half riser, moving the bars seven eights rearward.
The biggest thing for comfort has been just riding to toughen up. Often we see talk of a new seat at the beginning of the season or when someone gets a new bike. A few weeks of riding and a new seat and miracles have happened. I'm one that doesn't think those $500 seats get all the credit. Lambs wool or a bead seat can help that hot seat and riding can help the cramps. Would I buy another? Probably, but I have spent a lot of money on comfort including a trunk with a large back rest for the wife.
I drove through your area this spring on Rte 30 on the way to Dayton Ham Radio Convention. I live in a farming community just north of Warren. If you get over this way send a private message, we can have a cup of coffee.