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I've owned my 1990 928 S4 and used it as a daily driver (unless there is snow or ice on the ground) since I bought it in 2009. I have taken a number of 1000 mile round trips and one 3000 mile trip from home to central Montana and back. It has performed well and not left me stranded ever. I bought mine for $7,800 with 172,000 miles and just turned 203,000 a few weeks ago. It did have a fair amount of deferred maintenance to catch up but I have done everything myself and it has been pretty straight forward. The drive train is no more difficult or costly (in Porsche relative terms) to maintain than any other car I've owned and is way more reliable if water pump and cam belt maintenance is kept up with. The electrically driven ancillary systems can be a challenge to troubleshoot but there is a wealth of information and expertise freely shared on the major forums (Rennlist, Pelican, etc.) As far as oiling issues go, the issue of oil ingestion via the stock crankcase breathing system typically only rears it's head on the track when engine RPM's are above 5500 during or on exit from long left hand turns. If you intend to track the car much then installing one of the aftermarket breather solutions is a good idea. The only other "killer" issue is thrust bearing failure in later automatic transmission cars. This is easy to check during a PPI and easy to avoid with a quick bit of preventive maintenance if no damage has occurred.
As someone said earlier, buy the best maintained, documented example you can afford and keep the maintenance up and it will reward you with more torque-induced smiles than you'll know what to do with.
Mike
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