I don't know of any way to get around the object boundary. All I can say is bring your lettering down as close as possible then use Alt + Page down key to fine tune the touch down. I find it best to go to the right viewport and zoom in close between the two objects. also the underground visibility button helps.

"...I have forgotten how to align things properly with the view/camera."

Oh yeah, your camera is not aligned so you may have to set it up as we spoke yesterday in that other post...it really helps. ;)