Ben, you are the pessimist :-)
200-300 words in the lexicon suffices for successful hitch hiking travel. It is not the hard work. 1-2 months of easy work at leisure time.
Danger of a hitch hiking is strongly exaggerated. I am hitchhiker more than 10 years. I feel bigger safety on a road, instead of in Moscow.
But talks about hitch hiking beyond this forum. I am ready to discuss details , on other resource with that who are interested.
I'm not a pessimist, I'm a realist, if one was trying to buy travel insurance and the insurance company asked me how I was travelling and I told them hitch hiking, do you think they'd insure me ?