#235: Anna has made the leap to self-employment … but what’s next? She lives in the Bay Area and she’s trying to choose between five business ideas; she needs to make enough money to stay in her high-cost area. Doug recently won $9,000 from an online poker side gig and is wondering how best to use the funds: pay off high-interest student loan debt, or keep it to increase his poker earning potential? Alex and his partner want to househack a single-family property with a mother-in-law suit. What should they consider as far as zoning goes? Darrell is on track to retire in two years at age 55 and wants to know what he should do with his primary residence. Should he rent it out? Or should he sell it and use the profit to invest in rental properties? Or use the profit to buy his retirement home? Mara is curious about 1031 exchanges. She has equity in a rental property that she’d like to harvest, but she wants more information before making the move. Michael and his wife are struggling with competing goals. They want to invest in real estate, but they also want to move into an apartment closer to work to reduce their long commutes. Should they sell their home and invest the equity into a rental property, or should they take a HELOC on their home instead? For more information, visit the show notes at https://affordanything.com/episode235 Learn more about your ad choices. Visit podcastchoices.com/adchoices

#233: Deepak is considering downsizing his family’s home, but wants to know if the savings are worth the transaction costs he’ll have to pay. Anonymous and her husband hold $900,000 worth of privately-owned company stock. How should they plan for handling this money? Shelby is 25 years old and works for a company that awarded her restricted stock units. What should she do with these? Additionally, she traded in a 2013 Prius for a 2018 Subaru, for which she now owes $19,000. Should she sell it for a used vehicle or stick it out? Katelyn is interested in learning more about annuities. What should she know in order to make an informed decision? Max FI and his wife want to retire in 12 years. How should they invest to achieve this? Anonymous’s former employer offered a Roth and Traditional 401k, and his new employer only offers a Traditional option. How should he rollover his former Roth 401k? For more information, visit the show notes at https://affordanything.com/episode233 Learn more about your ad choices. Visit podcastchoices.com/adchoices