However..
Someone mentioned him as a possible POTUS. In that context, I would be pretty critical of him also.
After having known people with a gambling addiction, there is no way I could vote for him till I was sure he didn't fall into that category.
Aside from that, it's his money.. Let him burn it in the fireplace if he wants to. Hell, I don't care.
Strictly "Fiscal" conservatives (the type who always scream about the "immorality" of taxes, but support abortion.) in particular seem to have a problem with Social conservatives in general.
When one trips up, they are just waiting to smear him and scream: "See! See! He wasn't moral.. He was just like us! He just hid it better! He's no better than we are!"
And there's some faux Libertarian types who are simply jealous of anyone with money. Especially if they are perceived to be a hawk on conservative, social issues.