Well, gentlemen, I am updating this post just in case anyone comes across it on a Google search and are led to believe they also have a blown head gasket.
I took the bike to a mechanic to pull the motor and change the head gasket, since I have too much other stuff on my plate right now. He called me the next day and said that my front and rear cylinders both tested at 150 PSI, that he could find no trace of steam/white smoke from the exhaust, and that the bike felt great- no evidence of a loss of compression.
Greywolf, it would seem that your original observation still stands- you have yet to hear of a head gasket not doing its job on a Strom
The wet plug was from an over-rich condition from my power commander.
The low PSI test was because I didn't hold the throttle at WOT when I compression tested it (oops >.< live and learn).
The white smoke out of the left exhaust was because the bike had sat in heavy rain for several days on its sidestand, thus causing the water to pool in the left pipe/collector.
I still have no answer as to why the bike suddenly died on me back in February and would not restart until I pulled the plug and cranked the motor over a few times sans-plug, nor for why I found coolant (or water? I'm colorblind, so that's a toughie) in the oil when I drained it..
Anyway, here's the TL;DR:
I suspected a head gasket failure, took the bike out of commission for several months, took it to a mechanic and he found absolutely nothing with it. User error. The reputation of the Strom's head gasket has been restored. Rejoice, and be glad.