If you are fine with In place upgrade then it would cause you less trouble. It is easy, fast and doesn't require you to take backup [Though, I would recommend you to take backup]
One of the issue which I had faced was related to reporting server configuration which can be fixed by repairing.
Ensure that,
- You are migrating to correct edition
- You have fulfilled all requirement for MSSQL 2014
- You have installed related service packs
- You have ran upgrade adviser before going to upgrade.
That's all I have faced till now while migrating . :) all the best
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