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There are software packages available to educators that do this exact type of work. Have you taken a look to make sure that there isn't something that's already out there for your lessons? Often re-inventing the wheel is a lot more work than people think it is!
Let me be right up front, normally we're not about walking thru a project from the ground-up. Normally what we do here is help work thru the rough spots - think of this as you would "office hours" for a prof at university. What we are not is a code/application service.
With that said - many of us have a soft spot for teachers and non-profits/charities; especially, when the person we're working with is willing to put in the hours to build the project. Too much "good" comes into this world from the people in these positions to let them dangle in the wind.
Therefor, to give your project the best chance we need a lot more detail about the tools you have on hand. Basically, what you've done is walked into the First year primary English teacher's office and said you need help with your third year college mathematics lessons (well, some English teachers could do this...).
Better yet - let's start with some basic information to give our experts the best overview to see if they want to take on such a huge project:
- How strong are you in programing and database design?
- What programing and database languages/formats do you know?
- Available Operating system (Windows(version), Mac, etc)
- Available Software tools (OFFICE2016 Enterprise (32bit install) or you could be using OpenOffice, VisualStudio etc...)?
- What format are you using for your templates (Adobe, Word, etc...)?
- What format are your word lists in (CSV, XML, TXT, etc...)?
- You mention special Fonts: these are the hard ones as fonts are often system/OS specific and can be difficult to format on the fly. Some fonts are copyrighted for private/non-commercial use only which could preclude even educational usage without proper licensing.
- Graphics - here again we can get into some difficulties depending on the software being used and where the graphics are stored. You can also get into copyright issues so make sure you have that squared away before you start mass printing documents