We just went from an Work and Play 18 to a Fun Finder 27 toy hauler. We really liked to ease of the 18 but I got tired of having to take the bike out to use the entire living area and being just a little cramped . We put 18,000 miles in 2 summers on the 18 and had a good time. My wife liked the size of driving the 18 but we both like the separate garage and extra space for both storage and living. She did not want to upgrade until she sat in the larger trailer and reluctantly agreed it was nicer.
I would say go with the 26, not that much bigger but more comfort.
Mark and Joanne
2014 Fun Finder XT 276
2015 Ford F150 Lariat 3.5 Ecoboost 4X4 SCrew Max Tow
2011 Harley Road Glide Ultra