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#712: Jeff Hurst, CEO of Furnished Finder, joins us to break down what midterm rentals are, who they're for, and why now might be the best time to get in.

A midterm rental is a furnished unit rented for 30 days or longer - longer than a hotel stay, shorter than a traditional lease. Cities have been regulating Airbnb-style short-term rentals out of existence, leaving a wave of furnished properties with nowhere to go. That supply is now shifting toward the midterm market, driven by three primary tenant types: corporate and skilled trade workers, traveling healthcare professionals, and relocating families doing a "try before you buy" neighborhood test run.

We get into the specifics of what it costs to furnish a midterm rental (about $7 per square foot, compared to $30 to $40 for a short-term rental), where owners typically overspend (treating it like a leisure destination), and where they underinvest (quality mattresses, blackout curtains, kitchen functionality). Jeff also explains how to model out your returns, estimate vacancy, and use tools like Furnished Finder's market insights tab and AirDNA data to vet a market before you buy.

On the question of where to invest, Jeff walks through a layered research approach - starting with population migration, proximity to hospitals and universities, commuter corridors, and school districts. He's bullish on mid-sized cities with data center build-outs and expanding healthcare infrastructure, and argues that markets like those around northwest Arkansas, parts of Texas, and mid-sized Midwestern cities offer better risk-adjusted returns than the leisure destinations that dominated the short-term era.

Jeff also covers HOA red flags to look for, how to approach off-market deals, what the regulatory environment looks like for midterm (spoiler: almost no city is restricting it), and why the category today feels a lot like short-term rentals at their peak.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) Intro

(05:12) What midterm rentals are

(07:00) Why cities banned short-term rentals

(08:19) Who rents midterm — nurses, corporate workers, relocating families

(14:45) Extended stay hotels vs. midterm rentals

(16:34) Hospitality expectations for hosts

(19:22) How much to spend on furnishings

(21:02) Regulatory risk — nearly zero

(32:16) How to estimate vacancy and returns

(45:58) How to pick a market

(52:16) Why mid-sized cities win

(57:42) Following extended stay hotel construction as a demand signal

(1:13:00) Who owns midterm rentals — older than you'd think

(1:14:36) Why midterm feels like AirBNB in 2012
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#711: A computer science degree used to feel like a sure thing. Job placement rates topped 90 percent. Starting salaries cleared $80,000. You could do the math on your student loans before you enrolled.

That math doesn't work the same way anymore.

New York Times "Your Money" columnist Ron Lieber joins us to walk through what families actually need to know before borrowing for college.

He covers how to use the federal College Scorecard to look up earnings by school and by major.

He explains why the scariest student loan headlines are almost always about graduate school rather than undergraduate debt.

And he makes the case that liberal arts majors tend to catch up to their STEM peers by mid-career - even if the early numbers don't show it.

Lieber also makes a case that the financial return on college extends beyond salary data. Alumni networks, mentorship, and lifelong friendships all factor into the equation.

He suggests asking schools pointed questions about reunion attendance and alumni giving rates as a way to gauge how connected - and how useful - a community actually stays after graduation.

On the debt question, Lieber draws a clear line between federal undergraduate loans, which cap around $31,000, and the more dangerous combinations of Parent PLUS loans and private debt that drive the horror stories you see in the news.

He also addresses the community college path in detail - including what it actually takes to pull it off without losing time or credits along the way.

The conversation closes with a framework for parents: keep sparking conversations with your kids, stay curious about what they're drawn to, and treat yourself less as an advice-giver and more as someone planting seeds.

Share this episode with a friend, colleagues, and your college student: https://affordanything.com/episode711

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) No BLS jobs report today 

(01:41) Ron Lieber intro – NYT personal finance columnist, student debt expert

(02:41) College still worth it? Ron says yes, despite tough entry-level job market

(05:03) How to use the College Scorecard 

(06:27) Liberal arts majors often catch up by mid-career 

(07:17) The non-financial ROI of college 

(15:08) How much debt is too much? Federal undergrad cap is $31,000

(18:31) Community college as a launchpad; savings potential, but requires high executive functioning

(21:36) Scary student debt headlines are mostly about grad school, not undergrad

(24:39) AI and shifting willingness to pay; colleges facing enrollment pressure

(37:00) Financial aid office dynamics 

(40:39) Peak 18-year-olds; demographic cliff hits colleges differently by region

(45:54) Location matters; urban schools have recruiter and networking advantages

(54:11) Framework for parents and students; stay curious

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#710: What does it really look like to balance financial optimization with real-life tradeoffs—whether that’s choosing meaningful work, spending down your savings, or deciding where your next dollar should go?


Mike is planning to retire at 60 with $1 million saved and a clear goal: spend it all during his lifetime. He wants to know how to structure his withdrawals so he can maximize income now while still covering the decades ahead.


Kip was planning to retire after feeling burned out—until a chance conversation led him to a completely different role within his company. Now he’s happier than ever, but he’s also curious about whether real estate syndications are a smart next step for investing.


Jessie and their spouse are about five years away from early retirement and trying to decide where their next savings dollar should go—keep maxing out Roth IRAs, or shift toward a taxable account for more flexibility?

We’ll get into all of that—and how to think through each of these decisions—on today’s episode.

Resources Mentioned:

Listen to Kip’s previous question: https://affordanything.com/episode627

Don’t miss the YFRP Webinar! https://affordanything.com/rental2026

Join the YFRP waitlist:⁠ https://courses.affordanything.com

Stay in the Loop:⁠ https://affordanything.com/newsletter⁠

Die with Zero, a book by Bill Perkins: ⁠https://amzn.to/3P1ydBS⁠

Share this episode with a friend, colleagues, and your arborist: https://affordanything.com/episode710
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#709: Keith Wargo has spent decades navigating one of the most daunting financial planning challenges a family can face: raising a child with a developmental disability. He joins us to share what families need to know.

The financial stakes are significant. Keith, who is the CEO of Autism Speaks, estimates lifetime care costs for a person with a developmental disability can run between $1.4 and $2.4 million - and that figure may be conservative.

Yet many families put off financial planning because the day-to-day demands of caregiving leave little room for anything else.

One of the first things Keith walks us through is the federal benefits system. Medicaid and SSI are the primary lifelines for many families, but qualifying takes time - for Keith's family, it took three years of meetings and paperwork.

There's also a critical detail: SSI requires the individual to have no more than $2,000 in assets in their name. A well-intentioned inheritance from a grandparent can wipe out eligibility overnight.

That's why Keith recommends a special needs trust for most families. Assets held in the trust don't count against federal benefit limits. He also recommends pairing the trust with a "second to die" life insurance policy - one that pays out after both parents are gone - to help fund it.

ABLE accounts round out the toolkit. Similar to a 529 plan, they allow tax-free contributions of up to $20,000 per year for a person with a qualifying disability. The funds cover everyday expenses like food, transportation, and entertainment.

Unused 529 funds can also be rolled into an ABLE account, up to $20,000 per year.

Keith also addresses trustee succession - who manages the money after the parents are gone, and who steps in after that person.

His advice: start building a network early, revisit the plan every few years, and bring siblings into the financial conversation sooner than feels necessary.

Timestamps:

Note: Timestamps will vary on individual listening devices based on dynamic advertising run times. The provided timestamps are approximate and may be several minutes off due to changing ad lengths.

(00:00) The Financial Reality of Developmental Disabilities

(02:00) Caregiving's financial toll on families

(03:41) Keith's background

(04:26) His son AJ's diagnosis and journey

(07:08) Rights and services end at age 22

(08:06) Medicaid, SSI, and SSDI explained

(14:12) The $2,000 asset limit for SSI eligibility

(14:33) Why special needs trusts matter

(16:04) Life insurance as a funding tool

(23:08) Planning two retirements simultaneously

(25:04) ABLE accounts - the basics

(27:06) ABLE account balance limits by state

(36:35) Employment opportunities for neurodiverse workers

(42:11) Fraud and safety risks to be aware of

(51:15) Trustee succession planning

(53:22) Rolling 529 funds into ABLE accounts
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#708: What’s the smartest way to handle big financial transitions—when the stakes are high and the “right” answer isn’t always obvious?

Anonymous “Cyndi Jr.” is helping their 73-year-old mother relocate across the country and needs to decide how to use the proceeds from a home sale to balance long-term housing security with inflation protection.

Anonymous is trying to figure out how to handle quarterly estimated taxes on investment income—without relying on safe harbor rules that don’t always reflect market swings.

Luz, whose previous question was featured on the show, is now navigating a major job change and wondering what to do with an old 401(k)—while also rethinking how Roth accounts, an HSA, and debt all fit into a bigger financial strategy.

We’ll walk through each of these and help you think it through in today’s episode.

Resources mentioned:

Don’t miss the YFRP Webinar! https://affordanything.com/rental2026

Join the YFRP waitlist: https://courses.affordanything.com

Listen to Luz’s previous question: https://affordanything.com/episode583

Stay in the Loop: https://affordanything.com/newsletter

Share this episode with a friend, colleagues, and Cyndi Lauper: https://affordanything.com/episode708
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