Been flying a Dragonlady with a Saito 91 FS for several years. A good solid flying airplane. Dependable and predictable in the air.
Mine weighs 10 lbs and will float in nicely for three point landings and handles windy conditions and cross winds well. Wheel landings will need lots of room for roll out.
I wouldn't say its would be difficult to move up from a trainer, provided your a proficient flyer with the trainer. Its just different.
I'd suggest a buddy box and have someone good with a low wing tail dragger take it up the first time so you can become familiar with it's flight characteristics before having to take off and land.