How can I make the arrow inline with the text like my other headings? When I hit Enter above the arrow, it just pushes everything down and never actually lines up.

Are you trying to use the shape as a bullet?

And want a bullet in addition to numbering?

Not trying to use it as a bullet, just wanted it inline like the rest.

I'm not sure I understand what it is you want and what problems you are running into. See screen shot below. The attachment is a document with those lines.

Attached Images

00 deleteme.png (28.4 KB, 18 views)

Attached Files

deleteme.docx (20.4 KB, 9 views)

It seems like when I hover over all my other headings, the collapse / expand arrow is inline with the text. In the picture above, it is not. I guess it's not really an issue, but I was curious how to fix it.

OK we are talking different things. You are not talking about something that prints out but how they look in Outline view?

No, just how it appears on screen when you hover over the text.