1) Yes, The emails can also be sent directly from Filemaker
2) Yes, the file size limit is 4 gb ( Technical specifications of FileMaker Pro 14 and FileMaker Pro 14 Advanced | FileMaker ). Some files such as images can be compressed, others can't. Files stored inside the FileMaker database usually increase the database size by more than the size of the file inserted into it... which leads to my answer for #3.
3) Bad workflow... so many chances for database corruption in my view and then you both need to make sure who has the most up to date version, etc. Also you will very quickly get beyond the 20mb limit that most email clients put on attachments.
Put the file on a server or share it from a computer that is always on. You can have up to 5 people sharing a file at once before getting FM Server. There are hosting companies such as fmphost.com that can host the file for you also without you needing to buy FM Server.
5) For your case I would say yes. Only more advanced things like trying to run an AppleScript on a Windows computer won't work for obvious reasons.
5. There are some exceptions, font incompatibility may be the most issue. Os specific thing like "Send Event" script is nothing compatible.
Hello Carl and User19752 -
Thank you so much for your input regarding my issue - enlightening.