To downsize or not to downsize?

We have reached a stage when many of our friends have either downsized, are in the process of doing so, or moved closer to their families.
 
This has made us think. Ought we to move?
 
We got reminded of this dilemma today when we visited a friend who has downsized. She is delighted with her move though it involves an extraordinary amount of work.
 
Yes we know all the pros and cons. In our case it’s largely to do with the fact we live on a steep hill and in winter we can get snowed in, or a more likely scenario now with climate change, we get iced in.
 
The sheer upheaval puts us off and as long as we are fit and able we intend to stay put. 
 
Has anyone ever downsized and regretted it?
 
About the photo: Leo likes plant pots. He used to live in them until he came to us. So I was surprised to see him revert to this behaviour. (Maybe because I was sitting in his favourite outdoor chair).