Jenny Wahoske, a 35-year-old executive assistant who shares a car with her partner, has to be strategic to snag a parking space near her South End condo. She generally tries to run errands during business hours when it is easiest to find parking. If she has to leave home after 6 p.m, she generally walks or takes the MBTA — so she won’t lose her spot.
“I never plan that there will be a space for me,” she said.
But several blocks away, a Boston financial executive and his wife have permission from the city to park as many as 11 cars on the street at once. The man has residential parking permits for 10 cars, including two Ferraris, a Mercedes, and a Porsche, while his wife has an additional permit for her Volvo.
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Unlike many other large cities, Boston offers residents a parking permit for every car they own — with no limit on the number held by each household. As of January, there were nearly 94,000 residential permits in Boston, an increase of nearly one-fourth since 2006. Though most homes in Boston have just one residential permit, if any, the Globe found more than 300 have five or more.
Some say the practice makes the city’s notoriously tight parking situation even tighter in some neighborhoods. “The permit system is broken from top to bottom,” said Mark Chase, who teaches transportation planning at Tufts University, noting there simply is not enough space for all the cars permitted to park on the streets. “By issuing an unlimited number of parking permits for free, you are not managing the parking. It creates scarcity.”
James E. Gillooly, the city’s deputy transportation commissioner, said the city has no plans to limit the number of permits given to a single address or household.
“We haven’t reached the point where we think we should be rationing spaces,” he said.
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The city first designated a handful of streets for permit parking three decades ago, starting with Beacon Hill. But the residential parking program has grown rapidly since. Now virtually every major neighborhood in the city includes streets set aside for permit parking, and tens of thousands of car owners have signed up for permits.
A permit only gives residents the right to park if they can find a spot. And that can be difficult at times in dense neighborhoods such as the South End, North End, and South Boston, where residents constantly feel like they are playing a game of musical cars — fearful of driving lest they give up their spot.
The city has not tried to count all the on-street parking spaces available. One neighborhood group estimated recently that there are 4,000 permits for 1,500 spots in the North End.
“It's frustrating when you come home from work and have to drive . . . for an hour to find a space,” said Ryan Kenny, who chairs the North End Waterfront Neighborhood Council’s parking committee.
The fight for parking is especially contentious after winter storms, when some residents use everything from trash cans to broken appliances to reserve spaces they have shoveled out. And the issue has sparked fierce debates over how many parking spaces developers must build when they erect new condos or apartments.
But some local activists say Boston has not developed a comprehensive system to address the parking shortage.
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“Much of what we are doing is Band-Aids,” said Joanne McDevitt, president of the City Point Neighborhood Association in South Boston.
To make parking easier for residents, some other cities have been much more aggressive about trying to limit the number of parking permits — charging escalating fees, limiting the number per household, or regularly checking to make sure residents still qualify.
Philadelphia, for example, charges $35 per year for the first permit, $50 for the second, $75 for the third, and $100 each for four or more. San Francisco issues no more than four permits per address.
Cambridge and Somerville, like Boston, offer an unlimited number of permits, but not for free. Somerville charges $30 per year per permit, while Cambridge charges $25 annually for each pass. Cambridge said it also checks motor vehicle records twice a year to make sure residents have not moved. Last year alone, it canceled nearly 1,000 permits.
It is not clear whether any residences in Cambridge or Somerville have five or more permits. Both cities refused to provide addresses for permit holders, citing privacy rules. Boston provided the information only after being ordered to do so by the secretary of state’s public records unit.
Boston has no plans to start charging for permits, said Gillooly, the deputy transportation commissioner.
“We are doing it as a public service,” Gillooly said. “We haven’t seen it as an opportunity for making money.”
Jessica Robertson of the Metropolitan Area Planning Council in Boston, said providing unlimited free permits adds to the parking shortage.
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“If you have no pricing and no limits,” said Robertson, “then you create a situation where people are endlessly circling, looking in vain for spots.’’
Instead of limiting parking permits, the city has tried to encourage more residents to walk, bike, or ride public transit to work to free up parking. For example, city officials are planning to use a federal grant to establish ferry service between East Boston and South Boston.
Some city residents probably would resist any effort to charge for permits or limit the number at one address.
William Sorel, who has five parking permits in South Boston with his wife and son, said he already pays enough in city taxes on his home and does not want to pay more to park.
Moreover, he pointed out that two of the five family vehicles (an old Buick and a motorcycle) spend most of their time in his garage, so his family is not taking up as many spots on the street as it might appear.
“I try to be a good neighbor,” said Sorel, an engineer.
Sorel said there are other parking issues he considers more nettlesome, such as people who take up two parking spaces on the street, either out of carelessness or to save a spot for their family.
“I see cars parked a week at a time without the courtesy of pulling forward and making space,” he said.
Sorel said he is also convinced that some neighbors profit from their on-street parking permits. They leave their own cars on the street, then rent out their off-street parking spots to nonresidents.
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“It’s fairly common knowledge,” he said, though the city said it has not received complaints about the practice.
Others with multiple parking permits defended their right to park more than one vehicle on the street.
Linda Holland, an administrative assistant for the city with one private parking space, has permits for four cars and one motorcycle at her North End address. (Until recently, Holland also had a permit for a sixth vehicle — another motorcycle.)
Holland said cars have always been a hobby for her and she is willing to spend hours finding spaces for her vehicles.
Holland said it would be unfair to punish her for her hobby by charging her for the residential parking permits.
“I pay my taxes. I pay all my bills. Why would you do that to me?” she said. “I am the one shoveling, moving my cars, and going through all the drama.”
Samuel E. Bain Jr., the South End man who with his wife has permits for 11 vehicles, did not return calls about his family’s vehicles. It is possible at least some of his cars could be mostly garaged elsewhere, but a Globe reporter spotted one of his vehicles, a GMC Sierra truck, parked across the street on a recent evening. His brownstone also appears to have one private parking spot in the rear.
And it is possible some other permits belong to residents who have moved out of the city, because permits are good for two years and the city rarely checks when residents move.
Boston officials said they typically confirm a resident’s address with the state Registry of Motor Vehicles when they first issue or renew a permit but do not have the resources to check addresses more regularly.
Still, some residents were surprised that anyone would bother to acquire so many permits, given the paucity of on-street parking.
“I have enough trouble thinking strategically to park my one car,” said Wahoske, the South End resident. “I have no idea what I would do trying to park 10 cars — especially during street sweeping season.”
Todd Wallack can be reached at twallack@globe.com. Follow him on Twitter @twallack.