Has it ever been proven that smoking grass impairs a pilot? I can't believe, after all these years, that it's still illegal....oops...was that out loud?
I got my tailwheel checkout in my Luscombe. My instructor refused to allow me to use grass until I was competent on pavement. His reasoning was that grass can make you "pavement shy." I had to earn the grass, in his opinion.
Compared to a Luscombe, the Cruisemaster is a hybernating bear. You really have to make a fuss with your landing to wake it up. This said, if you're used to a tailwheel aircraft with heaps of rudder authority, like a Luscombe, be careful with the 'Master - it doesn't.
I like to wheel land taildraggers. Although the 'Master will eagerly oblige, it bit me when I did a wheelie with a direct crosswind - those three tails make wonderful weathervanes. In heavy, gusting winds, within 30 degrees of the nose, I still prefer to wheel it on. In variable wind or crosswind, three point is the way.
One real hoot you get with a 'Master, compared to a low horsepower taildragger, is to trim it slightly nose low. It will lift off, three point, on its own. I restrict this little bit of old world elegance, however, to pavement or long grass strips. A couple of years ago I saw someone attempt this at Antique Airfield in a cabin WACO.....the results were neither pretty nor amusing.
Jonathan