Several of the early Presidents were very wealthy in terms of land ownership but were deeply in debt late in life, Jefferson, Madison, Jackson.
George Washington was one of the wealthiest men in America, perhaps the wealthiest in Virginia after his marriage, but he also suffered from agricultural losses.
Didn’t George Washington’s properties also include several distilleries, which provided steady income even in lean years? America was just making the transition from imported rum to domestically produced whiskey (and the tax wars which accompanied that).
It should be noted that Washington was a working farmer up until his death, which may have been hastened by an ailment neglected as he continued to work hard every day.