Paul,
With an IMC rating myself, these are the guidelines I follow myself for flights which are planned to be partially in IMC (mainly getting above cloud and back down through).
Cloud base forecast to be at or above the MSA, so that if the noisy thing under the cowling stops there is a chance to see somewhere to put down when you inevitably drop out of the clouds. Meteoblue is handy for finding out where the tops are so that you can have a nice smooth flight above the clouds and away from the scud runners
Obviously avoiding icing conditions, ideally between airports with ILS approaches, or if it is going to be a let down to recover VMC, somewhere there is plently of room and a good fix, without terrain or obstacles.
If you can buddy up with someone else who has an IMC rating, being able to share some cockpit workload is great will probably enhance the safetly levels as long as you are clear who is doing what.
Good thread to share some practical advice.