Author: josh
Many rookies get into real estate investing to pursue financial independence, and going from single-family to multifamily investing can be a cheat code for reaching your financial goals even faster. Today’s guest had a goal of 50 rental units that she was able to achieve in just four years, and in this episode, she shares how she built her real estate portfolio so quickly!Welcome back to the Real Estate Rookie podcast! Today, Jessie Dillon returns to the show to update us on her recent investments. Last time we spoke, Jessie had just closed on her fifth unit, but she has…
Ashley Hamilton had every card stacked against her in achieving financial freedom. She was a single mother with two children, earning just $20,000 per year working as a waitress, living in Detroit, one of the hardest-hit markets following the Great Financial Crisis.Sixteen years later, she’s making $50,000 per month in pure cash flow (and she has the receipts to prove it)!In Detroit, foreclosures were running rampant, houses were being repossessed left and right, but what could she do with almost no disposable income? Thanks to a $6,000 tax refund check, Ashley did what everyone told her not to do—buy a…
In This Article Short-term landlords might not be able to sh-sh-shake it off when it comes to the additional taxes they may be liable for. This follows the introduction of Rhode Island’s “Taylor Swift tax,” the nickname given to part-time residents who own vacation rentals. With other states following suit, tensions are escalating between local municipalities, brokers, agents, and the wealthy property owners they represent. What is the Taylor Swift Tax? The so-called Taylor Swift tax—officially known as the Non-Owner-Occupied Property Tax Act—will take effect on July 1, 2026. It imposes an annual surcharge on non-primary residences (i.e., homes not…
Ashley:Taxes might not sound exciting, but what if I told you there’s a brand new bill that could put more money in your pocket and change how you invest today? Tony:And today we’ve got two of the best real estate CPAs in the game. You guys might know them. They’ve written several books for BiggerPockets. They’re my personal CPA and good friends of BiggerPockets. But we have Amanda and Matt from Keystone CPA, and they’re here to break down the big, beautiful tax bill, what it means, why it matters, and exactly how rookies can benefit from it. Ashley:Welcome to…
The Federal Reserve has finally cut rates. Will mortgage rates follow? If you’ve been waiting to rate lock or refinance, is now the time, or does the market think we have even further to fall?With inflation coming down from past years’ peaks and unemployment slowly ticking up, the Fed made the decision everyone was waiting for: cut rates…cautiously. There are still more 2025 rate cuts lined up, but they may not have the effect on mortgage rates that many people think. Many expect mortgage rates could dip into the mid-5% range by late 2025—Dave isn’t so sure.Today, we’re giving you…
In This Article Every day in America, more than 10,000 people reach the age of 65. That’s a staggering number by itself, but the real tidal wave is still ahead. The population of Americans aged 80 and above is set to grow by 28% in the next five years. Demographers call it the “Silver Tsunami.” With this surge comes a problem: Senior housing construction is at its lowest level since 2014. Millions of Americans will soon need assisted living, memory care, or modern independent communities. That mismatch isn’t just concerning; it’s a looming disaster. Plus, nearly 88% of Americans over…
In This Article Imagine it’s 2019, and you’ve got a rental property that practically pays for itself. Tenants line up, rents climb every year, and cash flow feels like a given. Or maybe you were one of the lucky ones who flipped houses when material costs were low and buyers were eager—every deal looked like a win. Some of us even dipped into Airbnb when it felt like you could throw a futon into a spare room and instantly be booked solid. In today’s market, it can seem like everyone is squeezing into the same crowded lanes. While it feels…
In This Article The New York real estate community choked on their spreadsheets when mayoral candidate Zohran Mamdani proposed rent freezes on all rent-stabilized apartments. While his words were primarily aimed at the powerful Wall Street REITs and large-scale landlords that own thousands of New York City apartment buildings, the policy could be most severely affected by the many mom-and-pop landlords who don’t have the resources to weather the consequences of stalled rents amid increasing expenses. Should Mamdani win the November election based on his tenant-friendly policies, it could have wider ramifications in other U.S. cities. A City of Renters…
Dave:In the last few weeks, several reports have come out showing that the job market in the US is weak and it’s getting weaker and the labor market is tied to the housing market and to the overall investing climate in all sorts of ways. So today we’re diving into the latest labor news and how this will spoil. So today we’re diving into the latest labor market news and how it’s going to spill over into the world of real estate investing. Hey everyone. Welcome to On the Market. I’m Dave Meyer. Thank you all so much for listening…
In This Article If you hang out with real estate investors, you’ve probably noticed there’s a buzz in the air again about Airbnbs. The short-term rental (STR) tax loophole, the strategy that allows W-2 earners to classify rental income as “non-passive” and use paper losses to offset their active income, has sprung back to life. The reason is that 100% bonus depreciation is returning. Under the new legislation, qualifying property placed in service on or after Jan. 20, 2025, can once again be depreciated 100% in the first year. For high-income professionals, the savings can be substantial—sometimes six figures in…