#326: Anonymous is struggling with being too frugal, possibly to the detriment of her health. I mentioned in a previous episode that I struggled with frugality for a long time. She wants to know: in what ways was frugality a hindrance or an asset, and how did I get myself out of such a frugal mindset? John and his wife aren’t sure how much they should contribute to their daughter’s Ohio 529 plan. They want her to graduate from undergrad debt-free, but they imagine she’ll get help from scholarships and that she’ll work as a teenager. How much is enough? Rafael just got a job as a 1099 sales associate and is wondering how the heck to calculate what he’ll owe in taxes. Rafael has a second question: he opened an account at Vanguard in December 2020 and noticed that he could still contribute to that account for the first few months of 2021. Which year should he have focused on contributing to? Elizabeth has two rental properties: one that’s paid off and profitable, the other which shows a loss. If she put her profitable rental into an LLC, could she still combine the rent from both properties? My friend and former financial planner Joe Saul-Sehy joins me to answer another round of questions. By the way, if you have questions on business, money, trade-offs, financial independence strategies, travel, or investing, be sure to leave them here and we’ll answer them in a future episode. Learn more about your ad choices. Visit podcastchoices.com/adchoices

#324: Rob and his fiancé are grappling with what to do about her $400,000 of federal student loan debt. Should they pay it off immediately, or bank on a 20-year dismissal? “Nurse Dreaming of FI” isn’t sure what her family’s next financial move should be. She’s torn between investing extra money into index funds, or using it to buy a fix-and-flip. Her goal is to make work optional. Which path will lead her there? Daniel recently discovered the financial independence retire early (FIRE) movement and got a job earning $50,000 per year. He wants to househack a duplex to get closer to FIRE, but how the heck can he find anything in this seller’s market? Anonymous and her husband have 457s with the City of Chicago. However, they found out that Illinois has a horrible credit rating. How can they - and should they - protect their funds? How much should they rely on their pensions? Nick is curious: how have my views on wholesalers changed over the years, and why? My friend and former financial planner, Joe Saul-Sehy, joins me to answer these questions today. For more information, visit the show notes at https://affordanything.com/episode324 Learn more about your ad choices. Visit podcastchoices.com/adchoices