Netspectrum

Can I upgrade my 14 to 16 without issue? Or should I fire up a 16 and copy stuff over?

Any recommendations?

There have been reports of successful upgrade from 14.04 to 16.04.

However, that is not official supported upgrade path. In addition, the underlying technology is slightly different in 16.04. So we recommend you migrating your stuff over to a new 16.04 instance.