I decided to follow the advice here and start looking into better signal generators.
For the fun of it, just burning time this evening, I cut the power to the final, removed the collector pin, bridged the buffer to the output network without a single thought to matching them, and the output now provides a clean sine wave (not modulating yet) at about 20.3dBm. The signal looks nice, and so far nothing gets warm and the output is still giving me roughly 50ohm. Then, using a coax switch that shorts the unused antenna port, I connected the radio to a 50ohm load. The shorted switch port (assuming that shorted contact is a pickup loop) was connected to a 30dB attenuator I had on hand, and now im down to -72.5dBm into the spectrum analyzer. I am almost there!!!! Yes, totally wasting my time, agreed. It's been fun seeing how close I can get with whats available though.