I'm having this same problem. I've used OLLY for almost a year now. Still loving it. But as my student adding more subjects/courses, my Weekly View Printout is getting longer and the cut-off issue is getting more annoying. I currently ask my printer to print all 3 pages of the Weekly Assignments onto one page. That results in one paper with the Weekly assignment list "chunked" into three quarters. But at least I can see it all on one page. However, with the odd cut-offs, it's still confusing when just glancing at it. I've taken to crossing out the bottom subject that is cut-off by OLLY and then re-writing above the other section that holds that subject and coloring in a new header. It works for now, but I'd really love a fix to this.
I have the current OLLY version on my MacBook Air. Thanks.