Sorry about your parents, Boss.
Since you're genuinely asking for opinions..
I wouldn't say you necessarily come across as arrogant, but from all the posts I've read of yours, you seem to define yourself by your wealth, and expect others on this forum to do so, too. I'm sure there are many of us with "means", but few are so eager that it is the first thing others know. I wonder what you're trying to achieve with the constant mention of your means - why do you need to be known as the rich guy? I remember a while back there was a thread about betting with your son about going whY, and then losing the bet, and that is unthinkable, because did you know I'm so wealthy? etc. It seems a bit braggy, but also a bit insecure. I think everyone would still like you if you were just a guy. Even the whole generosity thing is just an extension of the wealth thing. It's great that you give money to charity, a lot of money, and yes, relative to your means perhaps comparable to what others give as a proportion of their means. Still, I think you have more to offer than money.. and the preoccupation with $$$ doesn't let that shine through as well as it could. I'm sure you've got much more to offer.
The restaurant gig does sound like a good idea - not for the money side of things, but because it would give you something else to think / talk about, and to relate to others about.
The idea of 'downscaling' is a bit of a cliche - it is still working on the assumption that the amount of resources someone has available to them makes them a different person. I think it reflects a belief that those that 'poor people' are not like you. They are, in all the important ways.. same anatomy, similar hopes and fears.. many of the same sorrows (like losing parents). Focussing on the similarities rather than the differences of those from different backgrounds would be more helpful in terms of what you are trying to achieve. Especially since the important ingredient in poverty, desperation will never be realised, because you always have a choice.
Perhaps the first challenge could be to spend a month on AFF making no mention of yourself as a man with means, or of dilemmas due to your wealth. This would allow us all to get to know and connect with the real you - your personality, talents, intelligence, sense of humour etc. much better.