I reckon it would be pretty easy to do if you spent most of your time flying a fixed gear C172 and then converted to the Cutlass. Everything would be similar enough that if you got a bit behind the airplane, the fact that your normal fixed-gear pre-landing checks worked the same way could lull you into forgetting the differences and not putting the gear down.
I find that flying the Yak 52 is so different in cockpit layout and procedures to the other planes I fly (C172 etc.), that the danger of inadvertently "using the other plane's mental checklist" is considerably reduced.