July 9, 2019 is coming faster than we think. That’s the day Microsoft will no longer support SQL 2008 and SQL2008R2. I know there is a thought out there of if its not broken don’t fix it but if your business depends on SQL Server running an unsupported version isn’t a good idea. On top of that the longer you wait the harder it will be to migration. Frequently software running on SQL will require a specific upgrade path and its possible you may need to jump 2 or 3 versions to get current making any migration take longer the longer you wait.
Its ok to ask for help Steve and I have lots of experience upgrading and migrating SQL Servers. Feel Free to reach out. https://stedmansolutions.com