Dougs headers

Agree on the steering box clearance not being an issue.

What kind of starter are you running? I have a lightweight aluminum one in my 67 Barracuda, 360/Torqueflite, and the starter cable attachment is nowhere a header tube. (TTI, not Doug's, but still. . . .) Your rubber cover won't last any time that close to a header tube.

You can yank on the trans lines and bend them out of the way with a little muscle power. That said, I agree they don't appear to be routed correctly. I can't really see mine from above too well, and it's been a decade since I put the headers on, but I'm quite sure I don't have a trans line running under the headers. If you have pre-bent set, I'd run them. If I remember, they should run between the header tubes and the block. But I'd have to jack my car up and take a look underneath to be more precise.

The headers will give your cruiser a lot more power, from low down to up high.