The big difference between a Chipmunk and a Yak in the landing phase is that the Chipmunk is a conventional gear (ie taildragger) and the Yak is not. Most civilian pilots trained in the last 30 years have started on tri-gear and consequently find it harder to convert on tailwheel (I know I did!). There's no real mystique about landing a taildragger, but it does require focus and even after many hours and many landings you still need to concentrate. The tendency to swap ends, the need to avoid having any drift on, the reduced forward visibility, the need to get the speed just right - all are factors that affect avery landing. Whereas a moderately experienced pilot could probably land a spamcan in his sleep.
I've only once flown a Yak-52 and I didn't do the landing, but it struck me that it felt very much like a bigger Chipmunk in the air - similar control weightings and cockpit feel (though rather more knobs and buttons). I didn't like the springs they put in the Yak's controls, but understood they could be taken out. And of course, both aircraft were for years the primary trainers for their respective military operators.
The big difference between a Cessna 152 or similar and those other types, is that the military wanted to be able to weed the less skilful pilots out by adding to their workload and seeing how they handled things, whereas the average civilian flying school wants to keep pilots in the training system and earning them money. So after a while, when we civilian pilots want a bit more of a challenge than flying our spamcan to the nearest airfield for a hamburger, we're more likely to find it in a Pitts, a Chipmunk or a Yak-52 than we are in upgrading from a Cessna 152 to a 172 or 182. And the other common factor those non-Cessna types have?
They're all capable of aerobatics - which is immense fun and makes a real contribution to improving pilot skills...