"He pays no tax" won't be a big deal since the Republican position has long been that tax breaks for Great Men are somehow good for the economy and therefore somehow good for everyone. "Terrible businessman" is the more interesting angle, but it will be covered up by the tax angle.
I think the most interesting angle here are the hundreds of millions of dollars of loans that will come due in his second term. That's pretty terrifying especially given that to get that amount of money would require questionable lenders.
