Migrating from SQL Server 2008 R2 to SQL Server 2014
Your plan sounds OK to me. I have written a detailed answer describing each step at upgrading from lower version of sql server to higher version.

To help automate most of the process use PowerShell dbatool written by Chrissy LeMaire [migrates over 25 components including databases, jobs , logins, etc]. Here is a small video as well to get you started and how it works.

make sure you do full regression testing as moving to sql server 2014, we got hit by the new cardinality estimation (CE) bug and had to use TF 9481 to use the old CE.