A decade ago, Karl Baudendistel moved into a Hudson Heights studio in a building that was then brand-new. His apartment — conveniently near the 1 and A trains — faced the sunny back, and only on occasion would he hear dirt bikes revving in the street.

“The people in the front of the building had a hard time with the noise,” he said, and he noticed more turnover among his front-facing neighbors than his back-facing ones.

Mr. Baudendistel enjoyed his modern kitchen, but not the leaks that started toward the end of his tenancy, at which point his rent was around $1,650 a month. As the pandemic dragged on, he started craving another room. “I would like friends to come over, and in a studio that was not feasible,” he said. “I wanted to host friends rather than meet in overpriced restaurants.”

And as he approached his 50th birthday last spring, permanence also became important. “I wanted more of a home — an apartment with multiple rooms that feels more like a house,” he said, where “you can get away from your bed and watch TV in the living room.”

But while he has lived in New York since he started at New York University in 1989 and has always enjoyed visiting open houses, he was daunted by the city’s prices.

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“I couldn’t get my mind around why somebody would spend all of this money to buy a place and then have a mortgage and a maintenance payment,” said Mr. Baudendistel, a former Broadway company manager who is now the program director for Explore New York, an affiliate of the nonprofit educational company Road Scholar. “Why pay twice for one apartment? I could pay one rent and be done with it.”

Still, a good friend, Michael McCoy, a salesman on the Cole Team at Compass, had long been keeping an eye out for “a Karl apartment,” and sending him promising listings.

“All of Karl’s other friends were buying,” Mr. McCoy said. “I said, ‘Why pay someone else’s mortgage when you could be paying your own?’”

Mr. Baudendistel discovered that he could upsize to a one-bedroom co-op and the monthly outlay for the mortgage and maintenance wouldn’t be much more than the rent for a comparable one-bedroom. He wanted to remain in Upper Manhattan, preferably near the A express train, in an apartment with Old World charm and a good kitchen, for well below $500,000.

When he saw some places in middling condition, he daydreamed about how he could renovate, although he wavered about the extra money and time it would take. “Redesigning a place really captured my imagination,” he said.

Among his options:

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