Having worked in Engine Design for 6 years, particularly looking at some of the sealing arrangements of Japaese engines - which differed somewhat from European (Leaky?) engine experience from my previous 15 years... - and I learned a few things.
Almost every joint on the engine has a "unique" parameter that must be resolved for the joint to work - foerever. (2 years, 5 years or 10 years isn't good enough). Paper gaskets, (dry) are good for some joints, but not all. Viton O-rings - correctly installed in correctly design joints are perfect. In fact they were preferred for must applications on an air-cylinder actuator for a HV circuit breaker that I designed in a previous job. (40 year life requirement - 10 year maintenance interval - ZERO air leakage in 1 year!). Viton is also oil and chemical resistant, and very long-lived. O-ring grooves allow a very high precision compression without excess local pressure, and with metal-to-metal mechanical loading. I'm very suprised at Ranger's experience with the diesel engine lift pumps, but he does mention the flange loading/bolt arrangememt being significant. Maybe good seals but bad installation design? (Flange stiffness and bolting arrangement, relative to dynamic loading?). Gasket designers particularly are challenged to get the right combination of seals on cylinder heads. I remember (vaguely) that there were at least 5 different sealing regimes built-in to car engine cylinder head gaskets - that took some development time to get right. But the requirement was "zero failures in 10 years/250,000 miles". The cylinder seal must withstand high pressures and temperature, and vacuum loading, at engine cycle frequencies and for engines from -30C to +130C. Water channels must contend with hydraulic and chemical conditions. Oil pressure and drain passages have different conditions to coolant passages. Gaskets must be hard enough to resist the dynamic loading between block and head - and in some cases apply a clamping force to Iron liners in an Aluminium block where the block may not fully support the liner at the top.
But a useful lesson was that a simple (not high tolerance groove in a flange - with the correct FILLED silicon seal - with an ACCURATELY applied section of the gasket material will form an excellent seal for oil pans, timing covers, etc. especially where the 2 parts are of different materials, temperatures and expansion coefficients. Excess silicon will cause leaks, insufficient silicon will cause leaks. But the key was that Japanese silicon was heavily filled with stabiliser powder, but European silicon was not. After a few years we stopped trying to develop a system with "un-filled" silicon, and reverted to Japanese (3M) silicon of various grades for various applications. (They need different production plants and the commercial quantities required for different technology are huge!).
Hope this is of interest?
K2.