For myself, I still do. The most recent was buying a bull dozer and backhoe from an auction eventhough I had zero experience operating any heavy equipment. I should note that for the first year using these I had noone else around me and on my own land so I was not risking hurting anyone else or damaging anyone's property other than my own.
I think it comes down the morality of making promises to other people and potentially not being able to fulfill them.
If someone asked me to do a project and after I explained that I did not currently have the skill set to do it but thought I could figure it out, and they still wanted me to take it on. Maybe I would consider it but that would be a big maybe. Honestly I am more the asker than the doer these days.