Earlier quoted context omitted.
It's not a strawman opposition when you see people you work with unable to re-enter the country, environmental leadership questioning the human role in global warming (or even the role of CO2 in warming!), members of organizations that openly identify with the Nazi movement as first tier advisors to the president, etc... This is not a strawman, this is real and it's worth fighting. So are the other things you mention…
Everyone is free to pick their fight, sure, but when people have accumulated great power there is great responsibility, no? And if these people come from a philosophical and cultural and political monoculture, I think it's reasonable to be suspicious about them. FWIW, I feel the same way about the energy execs and crooked politicians--except in the case of at least Trump, there is at least a mandate of government gra…
At the end of the day, I personally care about actions and how they stack up against my personal ethical and moral compass. You are obviously free to use whatever method you want to decide if someone is doing good in the world. And yes, Sacca is free to spend his money however he likes. I also support Rebekah Mercer's right to spend her money on vicious attack ads. I don't have to respect her for it -- regardless of who won the election -- and you don't have to respect Chris Sacca.
Regarding monocultures -- circumscribe a set tightly enough and everyone comes from a monoculture. I don't think Sacca is any less exposed to divergent viewpoints than the Mercer's are, to use a relevant example.
And finally, just to respond to your overarching argument that Sacca has some responsibility to use his money in a particular way. He may believe so, and that wouldn't make it any more your business how he does it. And if he chooses to spend it on wine, art, and yacht collecting because that's what he wants to do with it we can both believe he can do better (Larry Ellison, if you're reading this: you can do better) -- but the society we live in hasn't made us the arbiters of good billionaire behavior, more's the pity. :)