But his optimism isn't blind.
"There certainly are gonna be some failures, but we'll find ways to overcome them," he said. "The next five-year period is gonna be the true test."
If his optimism isn't blind, it certainly is shared.
"He definitely sees downtown in a way a lot of us haven't," said Brien Poffenberger, president of the Hagerstown-Washington County Chamber of Commerce. "What he's doing will define the vision for decades."
Poffenberger was quick to point out that Deming's timing is right - that others have caught a new view of Hagerstown, too.
"Right beside him is Don Bowman," Poffenberger noted, who is redeveloping three parcels on South Potomac Street.
Bowman already has built a parking deck behind them, and said he plans to fill them with restaurants, office space - and one penthouse apartment. He anticipates work will be completed this summer.
Bowman, who announced his projects before Deming bought the adjacent property, said he decided to tackle them because "I was born here, and I thought it would be nice to do something downtown. I think it's a very vital part of Washington County."
Few have been more excited about what developers such as Bowman and Deming are doing downtown than Deborah Everhart, the city's economic development director. She said Deming's company, Demcore, "has seen the potential of our downtown and pursued a strategy of property control in the Arts and Entertainment District to catalyze revitalization," she said. "They purchased six substantially vacant buildings within one block of the Public Square, and have one fully occupied and one under renovation and close to being fully leased."
One of Deming's goals has been to bring more nightlife and entertainment options to downtown Hagerstown, and to that end, he organized a daylong "Downtown Live!" concert event last fall. But when he first proposed it, some Hagerstown City Council members were cautious. Councilwoman Penny M. Nigh objected to the sale of alcohol, and Councilwoman Alesia Parson-McBean questioned whether the event was to promote downtown revitalization or Deming's business.
"My business is the revitalization of downtown," Deming replied.
Ultimately, he got the city's blessing. And he understood the caution.
"It was new. It's always difficult for the first time," he said. "The city supported me as much as they could ... there's questions that they have to ask."
Deming hopes the optimism that he, Bowman and other developers have for downtown Hagerstown will be infectious.
"I hope others will jump in," he said. "The more the merrier."