Craig,
Once you have rotated the text in your textbox you can go to the drawing
toolbar click on Drawing, choose mirror and rotate and mirror
vertically/horizontally as needed. Or better still just rotate your textbox
using the rotate handle (green circle).
As to the other problem, you have two possible solutions, first use WordArt
instead you have a vertical text direction style there. Or use the vertical
text button on the WordArt toolbar.
Or format your text using shift+enter between eacht letter of the box.