Just an update. Thanks again for all the insight, and encouragement! After reading this whole post, I won't be able to respond to each individual reply, so please forgive me! I have smoked a tin of Early Morning Pipe, along with random other bowls of non-aros. I have found that with the standard packing I was doing the tobacco would almost never truly light, and I had to tamp a ton in order for the flame to take. So I began packing tighter. Actually probably using double the tobacco I previously would, and magically my tobacco light almost by itself! Keeping it lit for longer than 5 minutes also happened occasionally (far more frequently than before), making my realize how much practice I need tamping. I did still end up with about 1/4 of the bowl left that would not light, but it was not due to moisture in the bowl. In fact, I had almost zero moisture in the bowl (enough to see some in the draft hole, but no gurgling). No to figure out why that last bit won't take a light if it isn't due to moisture. Progress... finally! And who would have thought that I was packing too light for the tobacco to even take the light. Another problem I encountered though is realizing how much smoking outside increases difficulty. No only because of the wind factor, but also because being unable to visibly see smoke upon exhaling, I tend to over sip.
Also, going into smoking sessions already relaxed (or as relaxed as possible at the time) has helped as well!
Thanks again y'all!