Id like to be able to see at least 120kt GS into a 20kt headwind, which I regularly encounter flying west from here.
Then you turn around and fly the other way. Your gonna mostly average your TAS unless the weather is being an asshole.
Anyway, I think you can get "I fly other peoples planes around" type of personal insurance, which could be a good idea if you are having issues with the risk factor.
You sound like a good dude, i'd let you borrow my plane if I had one