I complained directly to the FAA Administartor at Oshkosh in ~2006 that the FAA would not approve a 337 to add a 'pump running' light for our Cardinal RG.
About a year latter someone came out with an approvable kit. All it takes is to run a wire from the pump motor to an led on the panel.
We installed it right away. It's really important to have this modification in a Cardinal, and probably most other Cessna single retracts.
With respect to the OP's question, the gear on our '71 Cardinal isn't a nightmare, but it does cause occasional sleepless nights. Some of the micro-switches are almost inaccessible under the cabin floor.
Signature broke the nosegear doglink while towing our Cardinal a couple of years ago. Cessna charges $17000 for this part! Signature, with the consent of our regular mechanic, sent it out to some aerospace welding shop to be repaired. I don't know what this cost Signature, but it was less than $17K.
The most expense gear repair our club has had was close to $10K on our Archer to get a DAR to create one a time STC to helicoil the landing gear bolts on our Archer.
The best GA gear system I've flown with is on the Duchess. That gear wants to come down, and the airplane has to fight to hold it up. Cessna single engine retracts are the opposite.