...I think we've reached a tipping point where all the technologies which needed to be perfected have been, and now they are quickly dropping in price.
The efficiency and low cost of solar arrays is a good example.
The perfection of the ion thruster is another. They don't fail, even after years of exposure in space and thousands of firings (see for example the Dawn mission). That gives a spacecraft the ability to match orbits with just about any object within Saturn's orbit (beyond that point, solar power collection becomes less useful).
Life support systems have long since been proven good enough to be sustained in a vacuum for years at a time. If such systems are not fully self-contained (as the ISS is not), a craft can be easily resupplied using the same solar array and ion thruster systems. If the resupply craft is then tacked on board the main vehicle, it augments the main vehicle's power and ability to change its delta-v.
An ion powered craft is not limited to Hohmann transfer orbits and/or gravity assist, as more conventional deep spacecraft like Curiosity and Cassini have used. There are at least three opportunities for a hu-manned vehicle to resupply itself with water ice and olivine: in the asteroid belt, at Jupiter or its trojans, and at Saturn itself. In a pinch, ice can supply water, fuel, and air, and olivine can scrub carbon dioxide, so humans can potentially survive even if some of the systems on its craft fail.
Communications also are not much of a problem since NASA has kindly provided the solar system with an Internet-like communications net.
That leaves only the somewhat unknown factors of prolonged exposure to solar radiation, and prolonged weightlessness, but solutions for those problems have been proposed and debated for a hundred years. A person who launched for Saturn's orbit four years from now and returned to LEO twelve years later might be sterile, cancerous, and unable to survive in Earth's gravity... or perhaps not if one keeps some of the craft's water mass between the sun and the life support zone. I know I'd take that risk in order to leave as soon as possible, and others would quickly benefit from my experience.
As far as the money goes, one way I would improve my safety factor, lower operating costs, and allow for constant systems monitoring would be to make a large part of my Mission Control an open-source project, where geeks like me can make themselves useful in the knowledge that their spare time really counts for something. I'd generate revenue by producing science and reality entertainment, contracting for science projects and conducting experiments, selling ride-along space for others' experiments and observations, setting up a foundation for donors to support me, helping to build strategically placed resupply depots and improving the solar system's comm net, and allowing Democratic Underground to sponsor me.
Oh yeah, I've been thinking about this a lot, and for a long time. I'll only be crazy until I pull it off.
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