I have travelled extensively throughout South America, Easter Europe, Western Europe and Asia, feel a bit intimidated by Russia, but would love to explore, not just come in and out in a few days....any thoughts?
In many ways, Russia is not user-friendly for independent Western tourists but if you are a seasoned traveler, can manage some simple Russian (and make out Cyrillic letters), you should be all right in most places.
As a 70-year-old American woman, I've lived in Moscow for the past 22 years, I've traveled around Russia by train and took one 6-day boat cruise. I've also hosted many Western backpackers and travelers through Moscow, many of them going on or coming off of the Trans-Siberian Railway..
I do think you might get more out of your trip if you make some Russian friends in advance (online) and go visit or travel with them. You can find many hosts (for free) on hospitalityclub.org or couchsurfing.org in both the bigger cities and out of-the-way places. I can guarantee you'll receive great hospitality and have memorable experiences.
Depending on your interests, there is a lot of interesting history and rich cultural resources found only in Russia. The weather is fairly comfortable between April-October. After that, you need a real winter wardrobe, but you'll also see the "real" Russia and be able to understand the life and people better.
By the way, it's now possible for Americans to get a 3-year visitor's visa to Russia.
Good Luck. almost 5 years ago