I am new to both CrossOver and Personal Historian. After installing SAPI 5.1 SDK, this program seems to be running pretty well. I'd say Silver Medal due to some lag on keyboard input but having never used this program on an actual Windows-based computer, maybe that's normal. I haven't tried ALL the features yet but so far so good... including dictation!
For instructions on how to get SAPI to install correctly, please see the following thread:
http://www.codeweavers.com/compatibility/browse/name/?app_id=6400;forum=1;msg=70691
After installation, be sure to go back to the Control Panel tab, launch Speech, and configure the input/output settings.
It took me a while to find this solution so I hope this helps someone else!