The first 2 pictures look like a bad OH to UG conversion.

I'd tend to agree NORCAL.
What's with the box at the top of that run of EMT?.
Could be my eyesight, but are there a few black wires coming down along-side the pipe?.
There's a lot to be said for removing the old junk that isn't needed anymore too.
techie,
In the second pic, next to that last PAR38 spot, is that object that looks like a box (up on the roof) anything to do with the electrics?.
I sort of get the feeling it's covering something electrical.
In the 4th pic, I bet that roofing material is going to love cutting into that flex over time.

Do you mean the grungy white thing sticking up above the roof at the top center of the picture? That is one of those angled pole mounted flourescent fixture that you used to see at gas stations, and used car lots.. It's on a pole next to the building, and lights a parking lot.

You're not imagining things.. there are wires running down the outside of the conduit.. telco and catv.

The flex is a painted piece of SJ or SJO cable.. notice how it exits the bell box without any fittings..