Experience first-hand or via experts who repair them daily, the former can be done by owning the same car or brand for a longer while and spotting the pattern.
Prefer makes that have excellent rust protection and models with relatively low stress configuration engines rather than high performance models. The two latter are usually mechanically the same or mostly the same, but the latter of them receive much larger stresses in use and hence tend to fail earlier.
If you intend to modify the car, prefer older ones, because they have lower regulations, but this depends on the legislative area you are in as well. For instance cars with OBD-II are too new for engine upgrades almost anywhere.
Prefer makes that have excellent rust protection and models with relatively low stress configuration engines rather than high performance models. The two latter are usually mechanically the same or mostly the same, but the latter of them receive much larger stresses in use and hence tend to fail earlier.
If you intend to modify the car, prefer older ones, because they have lower regulations, but this depends on the legislative area you are in as well. For instance cars with OBD-II are too new for engine upgrades almost anywhere.