1. Get the costs of transport to LEO down to reasonable levels.
2. Establish a LEO space tourism industry.
3. Establish tourism and mining operations on the moon.
When all of this has happened, it will be easy to go to Mars. I don't want more flags and footprints that cannot be sustained long-term, I want real space infrastructure with heavy off-Earth industry. Going to Mars won't do it, but going to Mars will be a natural extension of a burgeoning space industry. NASA isn't interested in space for the common man, they just want their super-elites to go. I think we're on the verge of a revolution in space enterprise, Tito going to the ISS signaled the start. This was in spite of NASA, not because of it. NASA is paralyzed with beauracrat mindthink, they're not the same organization that put men on the moon 33 years ago.
There has been a quiet revolution under way and it consists of private, non-government organizations opening the space frontier. NASA is clueless and will be made irrelevant in short order. Here's some of the players in this revolution:
Space Adventures Teams with XCOR Aerospace To Develop Sub-Orbital Vehicle
The revolution is underway, it just doesn't make headlines, but it is going to shock a lot of people when it starts rolling.
Me either. Gravity wells are the enemy if you insist on using chemical propulsion. OTOH, the human body does not like long periods of weightlessness. So doing long missions aboard a space station gets you little in return except damaged hearts.
I guess more than anything, I want to see us get over our completely irrational fear of nuclear propulsion. Because with an Orion, say, there is no place in the solar system that we could not economically exploit. We could land and take off at will -- and at little expense relatively speaking -- on any planet or moon we wanted to, deep gravity well or not.
I know that may not fit in well with private efforts, but I'm just talking about what government can and should do, imo.