I've flown a freighter exactly once.
One day a few weeks ago I was plexing and had three faction frigates shot out from under me in about an hour and a half. And they weren't even close fights. It happens. So I thought to myself: This must be my lucky day. Let's try lo-sec hauling.
I flew back to Dodixie and found the Iteron Vs to be a nice, cheap 2 million. Wow, I didn't know that. I thought the V was all leet or something. I fit it with shield tank (Couldn't fit a Large Shield Extender; 3 Mediums would have to do!) and Warp Core Stabs. I loaded it with half a billion ISK of faction ammo and a Firetail (gotta have something to get blown up once I get there, que non?).
It's 10 jumps to Nenn; we have a full shield tank and warp stabs, and half a billion ISK in cargo. We've never done this before. It's dark, and we're wearing sunglasses.
So I set a course and hit it! All went pretty well. The agility rigs seemed to be working alright and aligning me tolerably fast toward the next gate. There was even a three-man gate camp half an hour earlier that had conveniently disappeared for me.
And then, in the middle of me aligning to warp to Nenn station, a pirate fleet landed on grid. They had at least 15 Wolf assault frigates with EWAR and logi support, all flashy red in my overview like Christmas morning.
Phew. If I had come through a second and a half later...I shudder to think.
Now if that ammo ever sells, that'll be another story.