Becca,
I am using OrchidWiz through Parallels on my Macbook.
It works just fine for the most part; but I did have issues with the Journal like you said. It was very confusing and happened over one year ago.
I contacted OrchidWiz and did a copy/paste of the actual "error message" and they helped me fix the problem.
I believe the location of the Journal was the issue and we had to change the back up location.
Furthermore, make sure your version is up to date as this may also have been an issue.
Sorry my memory isn't better but I can assure you it WILL work.
Currently, my only current Journal problem is that I can't add pictures since the new update...but I've been too lazy (busy?) to contact them for assistance on that one