On your '87 Softail, the engine breather vent is behind and below the oil pump. The air from the breather is routed into the engine air filter by a metal pipe and rubber tubing that runs from the breather vent to the air filter. It is common to get a bit of oil in the air filter because of this system. The system was designed to meet EPA regulations of the time. Since then, the breather system has been modified to allow the engine to breathe at the top of the heads instead of down low on the engine. This resolves some of the problem with oil getting into the air filter but it still does not eliminate it. The only way to eliminate the oil from getting into the air filter is to reroute the air from the crankcase breather vent to somewhere else. Most people just let it exhaust underneath the bike by putting a small breather filter on the end of a short piece of rubber hose connected to the breather vent.
Good Luck
Steve
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Harley's leak - it is a law and a requirement.
On a more serious note, check your PCV valve.
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