I have a family member who is a lawyer and who has a similar type of software setup. The biggest obstacle I notice in the legal industry is that many simply don't care. They actively dismiss software as being unimportant even though they rely on it every day. It's a very bizarre case of the legal industry hating the very industry that could help them.
Note: perhaps my experiences aren't representative of the industry as a whole.
Note: perhaps my experiences aren't representative of the industry as a whole.