What were some aircraft in history, military and civilian of all eras, that were problematic either structurally or becuase of unreliable engines?
The original Flanker-A development prototypes had structural design issues, afaik being the first (analogue) FBW fighter in the Russian arsenal I'm not sure if these were more structurally or avionics related, but it was redesigned and structurally modified to the Flanker-B that we know today. I think these also have automatic recovery systems which help them along, it's a superbly performing model but has a reputation for crashes, iirc three test pilots were killed during development.
The F-104 had an infamous stall issue at high AoA which might be considered a structural/design quirk, the T-tail had its airflow blocked nicely by its stubby wedge wings so it lost longitudinal stability. Crashes plagued its service history, particularly when loaded as a fighter-bomber in export nations. More a design problem, but earned it the widowmaker reputation in the Bundeswehr.
The Me-109 has two infamous design problems, being effectively a design based on the BF-108 up-engined with a 12-cyl high performance engine, the way my great uncle described it was like a hot rod where you get a civilian model and put a very big engine in it, so it was a real handful at low speed but handled extremely well at high speeds. This was part of the problem which caused so many accidents, quite a large proportion of all losses were within 1km of the airfield (not just due to the undercarriage during actual take off and landing). The weight saving feature of attaching the undercarriage to the fuselage was of course its other issue, it gave a narrow track and a wide splay which gave it ground spin problems early on, and when the DB605 was fitted it was very easy to pancake (due to torque) which was almost always fatal.
The Fokker Dreidecker had a habit of shedding the top wing in dives, one of the main advantages a/c like the SE5a had over it.
One of the other problems with the P-39/63 was high likelihood of fatality if the pilot rode them through a crash (engine would come into the cockpit). Similar problem with the DH2 from WW1 (pusher config, lots of runway fatalities).
Me210 had structural design problems until modified.
He162 infamously killed a British test pilot cited due to structural problems.
The P-80A had quality control problems for a while with its turbine blades which went undiscovered until several destroyed or removed the tail section entirely from the aircraft.