I think one major issue Trump might face is that the economy isn't really doing particularly well, if you're not already fairly well off. It's not Trump's fault, it's a system passed down from administration to administration and the rot started way back.
The low base interest rates essentially allows Wall Street to carry trades at little to no cost, sometimes at a negative cost. If interest rates to carry a trading position are lower than the rate of inflation then effectively they are being paid to carry open positions. At the same time Main Street faces marginally more realistic interest rates, meaning it costs real money to borrow and invest.
The stock market has hit record highs relentlessly since Trump took office but the stock market can be a fickle beast, and isn't a particularly useful metric to measure how the economy is doing from the perspective of someone who doesn't have the spare cash to invest in the market. It's also not much comfort to the person who sees stores closing their doors permanently, shopping malls containing growing numbers of boarded up stores and losing their anchor stores and the like.
One trouble with modern day financial engineering is that, if used unwisely, it can create an illusion of prosperity while increasing vulnerability to external shock events. For a time it was pretty much the done thing for a company that owned large swathes of real estate to sell them for a lump sum, then rent them back. Which is great, as long as the lump sum is used wisely. If the lump sum is used for little more than executive bonuses and stock buybacks, the company's cashflow is forever hit with additional costs, rendering it more vulnerable to a downturn in sales.
Of course none of this is the fault of whoever happens to occupy the White House at the time it all goes south but you can be sure that if it happens to collapse on Trump's watch (or if the powers that be can engineer a collapse at an electorally convenient time) the media will be very quick to crow about how the economic benefits of the Trump administration proved to be an illusion. I don't imagine they will say the same about the eight years of "growth" seen under Obama that did little more to help the people at the bottom than the "growth" under Trump.
