1283: Investing News from Chicago & Short-Term Rental Bubble? with MyLodgeTax's Rob Stephens

17 Sept 2019 · 34 min
Episode

17 Sept 2019 · 34 min

0:00

In episode 1283 of the Creating Wealth Show, host Jason Hartman and guest Rob Stephens (co‑founder of MyLodgeTax, an Avalara company) discuss three main themes. First, they examine Chicago’s real‑estate environment, noting Amazon’s expanding footprint, the city’s relatively low property prices compared with other “mismanaged left‑wing” markets, and the looming risk to California’s Prop 13 tax shield. Second, they analyze the short‑term rental (STR) market: its rapid growth, the balance of supply and demand, the entry of institutional players such as Marriott and other branded operators, and how economic cycles could affect occupancy and pricing. Third, they dive deep into the complex tax compliance landscape for STRs, explaining the myriad local, county, and state occupancy/tourism taxes (often 10‑23% or higher), the role of platforms like Airbnb and VRBO in collecting some taxes, and how MyLodgeTax provides a cloud‑based service to register, collect, file, and remit these taxes for hosts. Throughout the conversation, the hosts intersperse political commentary, cautionary advice about market manias, and promotional details about upcoming events and contests.

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