I owned 3 Checkmate's in 10 years in the late 80's to mid 90's. I had pretty close ties to the Comb's family. When I wanted to upgrade to the 30 Mr. Comb's suggested I wait a year until they we're launching the new 33 with a step bottom. By the time I was ready to place my order Checkmate stopped making the stepped 33. When talking to Mr. Combs he stated that the 33 stepped bottom was hard to control and was not working out to their standards.
I don't know how many stepped 33's we're built, but my suggestion would be, make sure your friend takes a good long sea trial before the purchase.
Don't forget about the 358 Sonic I have for sale. Your friend might be interested in the Sonic.