The Matrix Trilogy had an excellent line, that really isn't played up enough.
> There are levels of survival we are prepared to accept.
This implies the machines were ready to separate (some programs) into compartmentalized versions to ensure survival and to start over, as in the beginning of their ascension to dominate the earth's surface. This strategy seems particularly applicable to deep space exploration as it speaks to practicality and the machine equivalent of transhumanism.
A form of space ark is currently, our best bet. Haul organic material (maybe just DNA) or a machine capable of synthesizing appropriate material from raw materials and send it off, piloted by an advanced AI and + digital copies of human minds. Based on our current understanding of physics, people born in the solar system will never get out of the solar system. The idea of self-contained craft that "lug around" energy is really silly and prone to failure. It's incredibly risky and there's no good model for how to do it. When you take the idea of minimizing organic maintenance and we already assume we're willing to invest a relatively large amount of inorganic components, we have a couple near-practical solutions. After we arrive at a habitable planet, we have a new set of problems. Say there's (likely) a ubiquitous pathogen that our human bodies can't defend against in the planet's environment, we better have the technology to adapt our bodies. There's not as many hurdles to cover as one would think, they are just different hurdles than most people think about and it's within reach.