Not once. Tbf, I am considering the herculean task of getting off of gmail, but if I were to go with my own server the burden has basically nothing to do with setting up the email server (easy) as this post might suggest, but instead the burden and latent risk involved of having to be personally responsible for operating, maintaining, and being exposed to externialities (like 0days, being blocked by filters, server outages, etc.) Setting up services is trivial compared to the aggregate cost in time, money, and context-switching tax over time of operating them.
That's the part that I really don't understand. If the recipient hired someone to throw away their emails, why would that possibly be my job to rectify? I sent them a legitimate email, they hired someone who promised them to throw away spam, but obviously is incompetent at doing so, so it's up to them to hire someone else!?
I probably would have avoided ever getting dependent on them to that degree in the first place.
But, yeah, sure, I see the point--but my impression is that people automatically see it as their responsibility to figure out why someone else's email provider is throwing away their emails, regardless how much you depend on them.