Hi Gregory, I suspect any software would experience similar issues in version compatibility. It's important for these companies to show constant improvement such as bug fixes and added features, faster processes, which in turn makes our jobs better. If I were in your shoes, I'd have a heart to heart conversation with your board of directors, share your experience with them, and get a line item in the budget for software upgrades. I don't know your circumstance; you may be in a community theatre which is largely funded by donations. The world does move on, however, and if your goal is to be able to interact in an effective manner, then current and updated software is a must.
Peace, and best of luck,
Tim Olson