The late cars have an auto tensioner so it does help but with all 944 you must look after the timing belt.
FWIW my 944 has been great, other than routine maintenance I have replaced the clutch master and slave cylinders, dealt with a cracked starter solenoid but thats about it. I have also replaced shocks, springs, sway bars, every fluid in the car, wheels, tires, more wheels and more tires but thats a different issue.
I belive the issue and bad reputation of the 944 is created as a result of people who can afford to buy the car but then put nothing into maintenance. The next owner then ends up with a basketcase or endless "deffered maintenance" which really doesnt make for a fun car and hence the "944s are bad" reputation gets built. Unfortunatly the 944's low price may be its demise. I think the 914 is the same, great car but just try and find a decent one now.
I have had my S for 3 years an 8v for just a year (rear ended and writen off) and I really like the cars. I could buy a boxster or a 911 but I find the 188hp is adequate and I like being able to not give a second though to loading up 4 tires in the rear driving 3 hours to an AutoX, compete and drive back while not breaking the bank. I have also used my 944 for work, driving 1000+Km per week, and found the car comfortable and perfectly suited as a daily driver.
Looking for a 944 I would suggest that maintenance records are a must have, Aside from the ussual used car things I would pay particlular attention to the timing belt, power steering leaks, and clutch.
I have also had 2 e30s and think they would be a decent first car as they are still fun and mechanically are fairly simple. You still have the timing belt issue and its still a nearly 20 year old german car, they arent '07 Corollas!