The Ascender and Descender, as positive values, don't add up to the UPM; also check your bbox values.
For some reason in Illustrator I'm getting a giant cursor where text is added to the top. If you look at the picture you'll see the black portion is highlighted text. Despite the huge cursor the leading appears to be perfectly fine.
I'm not sure if this is related, but the ttf is cut off in MS Word and I'm assuming my vertical metrics are off...which is at least one of my problems if not both.

And for my dimensions:
Asc: 590
Des: -287
UPM: 1000
I've read the numerous articles about vertical metrics but something must still be off. Based on these values can anyone lend a hand on my OS/2 and hhea?