Yes, this matters
https://fivethirtyeight.com/features/how-trumps-tax-returns-could-affect-the-election/?ex_cid=538email
"In May 2019, after The New York Times published a report that showed Trump had lost around $1.2 billion between 1985 and 1994, public polling found the story could lower public opinion regarding Trump’s business acuity. In a Politico/Morning Consult survey, 54 percent of voters said Trump had been a “very successful” or “somewhat successful” businessman, while only 36 percent thought he’d been unsuccessful. But after being presented with information about Trump’s financial losses, the share of voters who thought he’d been a successful businessman dropped to 43 percent. And that slide was felt across the board, falling more than 10 percentage points among Democrats and Republicans, and 8 points among independents. Meanwhile, another May 2019 poll from Fox News suggested that evidence against Trump’s business savvy could influence the attitudes of a small but meaningful share of voters: 20 percent said there was a “strong” or “some” chance that new revelations could affect their views of him.
That 2019 polling squared with findings from a study by political scientists at the University of Maryland, which found that voters’ opinions of Trump’s business skills fell among both Democrats and Republicans when told how Trump had benefited substantially from his family’s financial help. The study showed that a lack of knowledge about Trump’s background mattered to how Americans perceived him, as a sizable share of Americans — around 40 to 50 percent — didn’t know that Trump grew up very wealthy and received millions of dollars in financial assistance from his family. If respondents had fewer misperceptions about the president’s financial background and the aid he received from his family, they tended to rate his business competence more poorly, the study found."