Good report dude! I have to agree with the above comments: find some waterproof boot covers. I did the Alaska thing and even if it was not raining, they made a big difference in lowering the convectional heat transfer. you also may want to consider taking off a layer of socks... My time climbing mountains has taught me that there is a goldilocks zone for number of socks to keep your feet warm. Too little and you obviously have no insulation. Too many and the fabric gets compressed inside your boots and air doesn't get heated up because the material can't "loft" and reach it's insulating specs. okay okay. I nerded out on you there. But I'm also a 25 year old ME with a bike, so I can relate. Also, a note on the loneliness: Persevere. It is going to come and go, but you always get through those dark times. By going alone you also have the benefit of being more "approachable" when you stop somewhere. I've traveled alone for.... 2 years? There are some viciously dark times, but you always come out on top and there is no lack of good people out there to help you out, whether you know them or not. Good luck!