Seems to me that maybe we've been aiming too high, right now. I've tried any number of times to get elected to public office at the state level, and once at the city level, all unsuccessful. No money, no organization, etc.
But I have been successful at the very local level - Home Owners Association. I've been elected 26 times (more or less (I've lost track)) as treasurer of our HOA. Yes, it's very small (6 units); Yes, no one else wants the job. Any yes, I did it before I knew what a libertarian was. I did it for a very practical reason - I wanted to make sure my money was spent wisely. But it has given me very practical experience about what's possible, and what's not, and how to deal with the public.
So, my advice to Libertarians, and libertarians, who want to get some practical experience winning election campaigns and learning to govern, is to get elected to your home owners association, or your neighborhood busybody group (maybe you can prevent them from doing something stupid by actually serving on the board as a voice of reason).