Let's get the good stuff out of the way. I think the 944 is one of the prettiest cars ever built; I love the looks and the handling. The galvanneal body lasts and lasts.
That being said.. I have had four different Porsche models over the years from a 356 to a 911, not all of them old. I have found them to be overpriced when new, very expensive to maintain, and in some respects cheaply made. I will explain.
The electrical system is second only to the infamous Lucas Electric in unreliability. The gauge of wire is on the edge of acceptable, and since resistance increases with temperature, a point comes where it is inadequate and the wire overheats, the insulation hardens, breaks, and short circuits occur. Additionally, the switches utilized are under designed, either failing outright or developing internal resistance (such as the washer switch).
As time has passed, the routine maintenance expense has increased, in direct opposition to other manufacturers. Changing oil in a 993 is a nightmare, not to be attempted by the faint of heart. In the 944/968, most routing maintenance is relatively straightforward, but this is the last Porsche model for which this can be said.
The 944 engine is reliable, as long as it is properly maintained. A failure of the timing belt is a disaster, which can result in a rebuild which will exceed the value of the car. Oil seals are a problem, particular those on the external oil cooler. Ignored, water will enter the lubrication system and destroy the bearings.
One has to remember that Porsche is a small company, and therefore does not have the ability to change poor designs as quickly as larger manufacturers. Therefore, the stubborn adherence until recently to air cooling in the 911 models (left over from the Volkswagen roots.. sorry, folks) and the development of the timing belt system in the 928/944 which requires a $400 tool to adjust.
In conclusion, had Porsche not become greedy, continually raising the price of the 944/968 to a point where it was no longer an entry level vehicle, and had they developed or borrowed a more versatile engine, this vehicle could have developed into an outstanding competitor as well as a comfortable cruiser.