The “Boring” Rental Strategy That Could Retire You by Your 40s (Rookie Reply)

Real Estate Rookie

BiggerPockets

Entrepreneurship, Education, Investing, Business, How To

4.7 • 1.8K Ratings

🗓️ 20 March 2026

⏱️ 23 minutes

🔗️ Recording | iTunes | RSS

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Summary

Do you dream of reaching financial independence (or retiring!) in the next 20 years? Whether you’re in your 20s, 30s, 40s, or 50s, it’s never too early or too late to buy rental properties. Today, we’re sharing a clear, 20-year roadmap that could give you a sizable real estate portfolio and more than enough cash flow to live on! Welcome to another Rookie Reply! Today’s first question comes from the BiggerPockets Forums, and it’s from an investor who’s been priced out of their own market. Where should they start their search for more affordable home prices? We point them in the right direction while also warning them of “cheap” properties that aren’t worth the risk. Next, we hear from a young couple looking to achieve financial independence in 20 years. Should they buy a home or a rental property first? What investing strategy will get them closest to their goal? Another investor is worried about short-term rental laws derailing their deal. We show you where to find your city’s latest regulations so you can make the right decision! Looking to invest? Need answers? Ask your question here! In This Episode We Cover Our 20-year roadmap to achieving financial independence with rentals Whether you should buy a house or a rental property first (or both!) Where to invest when your own real estate market is too expensive The types of rental properties that give you the least appreciation (must avoid!) How to do your due diligence on a short-term rental market And So Much More! Check out more resources from this show on ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠BiggerPockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ and ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://www.biggerpockets.com/blog/rookie-694 Interested in learning more about today’s sponsors or becoming a BiggerPockets partner yourself? Email ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠advertise@biggerpockets.com⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠. Learn more about your ad choices. Visit megaphone.fm/adchoices

Transcript

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0:00.0	What if the biggest mistakes in real estate don't happen at the closing table?
0:03.9	They happen in the three decisions you make before you even write up an offer.
0:08.4	Today we're answering three questions straight from the Bigger Pockets forums that every
0:12.4	rookie has to work through before deal one.
0:15.1	How to pick a market when your own backyard doesn't pencil, whether to buy a rental or a
0:19.4	primary residence first when you're just starting out, and what you actually need to know about short-term rental regulations before you
0:25.9	bet your strategy on Airbnb.
0:33.3	This is the Real Estate Rookie Podcast. I'm Ashley Care.
0:36.6	And I'm at Tony J. Robinson. And with that, let's get into our first question, which comes from the Bigger Pocket's forums. Now, this is a longer question, so I'm going to paraphrase a bit here. But the question that basically says, I'm an aspiring investor living in Los Angeles, and investing locally is basically out of the question. Even a house hack in this city is tough right now. Anything with an
0:55.5	ADU or multiple units in a decent area is well above the $1 million mark. So I'm stuck at the
1:01.0	stage of choosing a market. I'm looking for out-of-state opportunities where I can actually cash flow.
1:06.9	What criteria should I be using? And how do I narrow down from the entire country to one place that I can actually commit to?
1:15.9	It's a great question.
1:16.8	And it's one that a lot of Rikis honestly gets stuck on initially is where do I invest?
1:21.8	Now, I'm just going to talk strategically here for a moment because I think it's an important foundation to lay.
1:27.3	There are over 20,000 cities in the United States.
1:31.2	20,000.
1:32.5	So the chances of you finding the Goldilocks city that is the absolute perfect match for you, right?
1:39.8	Or like the Cinderella slipper where it is the absolute perfect city for you, it's going to be tough.
1:46.2	Right? With 20,000 cities, there are probably hundreds, if not thousands of cities that you can
1:50.5	invest in that would make sense to help you achieve your goals. So the thing that you should be
1:56.1	focused on is not what is the absolute best city for me to invest into? The thing you should
	...

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