He has money. He pays lawyers and accountants to figure out loopholes and hide his assets, just like every other rich asshole. He doesn't know how to do any of that shit on his own. What was it about his real estate deals in NY that gave you the impression he was savvy? For starters, it's really easy to make money when you have a lot of it already, and somehow he repeatedly invested in projects that were obviously destined to fail. Not to mention, most of his actual monetary gains came from leveraging his name, which he could do because he was famous, and he was famous because he was rich enough to just choose to be famous. He also started with enough money to pay others to figure out how to turn that money around and make more money, and he still repeatedly botched it.
He's able to sway voters, sure, because he follows the applause, and when his actions or words garner less applause he denies he did or said them. That's not playing any sort of game; it's animalistic instinct, reacting to praise. He blundered into a demographic nobody else was willing to touch because of the toxic shit they believe, and because he was in the right place at the right time an entire political party reluctantly fell in line behind him. Sure, you could interpret that as genius, because conventional wisdom stopped everyone else from doing it, but it just isn't accurate. He has an insatiable ego and no standards of decency, which invigorated a race of subhumans nobody else had been willing to entertain, and a lot of other people jumped on board out of desperation or opportunism because there's a lot wrong with our culture and not a lot of politicians addressing it.
I don't think you're complimenting him. It sounds like you're rationalizing because it's difficult for the human brain to accept that someone so dim-witted could succeed so often. And that's reasonable, but I promise there's nothing to underestimate. The risk is in attributing strategy to chaos, and overestimating the intention behind his actions.