It's definitely doable, even a much less expert pilot like me. Flying a smaller ship like a Cobra surely helps but more essential is patience and situational awareness. Always glue an eye on the radar for the whole docking process and only enter the toaster if no other ships seen on the other side in your flight path.
Quiet another story and way more dangerous was my first encounter with an AI pirate. I usually submit to AI interdictions since I'm doing short-mid range exploring, rares trading and some (random) bounty hunting all in one go. My ship is well fitted for this role but of course no battle tank. Risky and not efficient but feels as if the game was specifically made for this playstyle in mind. From my first 200Ly with rares on board I had my first encounter in 1.1. A surprisingly for its low rank tough and nasty Eagle that shamelessly aimed for kamikaze curse. Two times I could smell the socks of the AI pilot (awesome sound btw at these close encounters. Big kudos to Sound department!

). I guess I was VERY lucky this time...
tl;dr
Doesn't mean I support the current state where smaller ships do more damage to bigger ships. No one sane in its mind can simply ignore that nonsense. In general I would LOVE such a harsh collision detection but with the more sane idea of 'more mass = tougher structures = dishing out more damage in a collision'.