When I first moved to New York, I thought finding a place would be tough—but not that tough. I was wrong. Between hidden fees, listings that disappeared in hours, and landlords who never replied, I was constantly second-guessing everything. I wasted weeks crisscrossing boroughs, chasing apartments that looked nothing like the pictures, and dealing with brokers who barely listened to what...

The first time I had to deal with a sidewalk violation in New York City, I treated it like a minor errand—one phone call, maybe two, and a patch job later, done. But that assumption cost me thousands. Not only did I get hit with a second DOT notice, but the contractor I had rushed to hire disappeared halfway through the job. It took weeks to fix, cost double what I expected, and stressed...