I think I may have finally solved the problem, and it looks like Word is keeping my settings as default which is good!

To print to BOND ENVELOPE from ENVELOPE FEEDER:

1) Click Mailings
2) Click Envelopes
3) Click Options
4) Make sure Envelope Options tab is showing the proper envelope size (4 1/8 x 9 1/2 in my case or 4.12 x 9.5")
5) Make sure PRINTING OPTIONS tab is set to FEED FROM ENVELOPE FEEDER

Thanks!