Relatively new to real estate investing, eager to learn

Investor · Bandon, OR · Member since 2025 · 4 posts · 6 votes

Hello, fellow real estate investors. I am Chris Cline from Bandon, Oregon. Real estate investing relatively new to me and I’ve decided to begin my journey with Airbnb arbitrage and house hacking. I have been researching and underwriting LTR properties in many different U.S. markets for the past eight months while working full time. I have struggled with analysis paralysis since pretty early on and I’m learning that financial decisions are not my forte, but I am determined to become a successful real estate investor. Any and all advice welcomed and appreciated.

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Troy Christiansen

Member since 2025 · 4 posts · 12 votes

Thanks for sharing your story, Chris. It sounds like you’re doing a great job getting educated and staying motivated, which is half the battle. Analysis paralysis is super common for new investors, but it’s usually a sign that you're ready to take action, so the next step is to help yourself with a final push to move forward. I’d recommend giving yourself a firm deadline to at least try making your first offer. Even if the deal isn’t perfect or doesn't go through, the experience could be worth it, and the next time will be easier.

Since you're focused on Airbnb arbitrage and house hacking, you may want to start with markets where short-term rentals are allowed and don't have too many significant barriers to entry. Several areas either don't allow it or require a permitting/licensing process, so make sure to do your research on that aspect before you move forward. Also, when looking at house hacks, duplexes or triplexes can give you a great mix of cash flow and lower living expenses. Keep it simple, keep learning by doing, and take things one step at a time. Best of luck to you!

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Troy Christiansen
Member since 2025 · 4 posts · 12 votes
1y
Thanks for sharing your story, Chris. It sounds like you’re doing a great job getting educated and staying motivated, which is half the battle. Analysis paralysis is super common for new investors, but it’s usually a sign that you're ready to take action, so the next step is to help yourself with a final push to move forward. I’d recommend giving yourself a firm deadline to at least try making your first offer. Even if the deal isn’t perfect or doesn't go through, the experience could be worth it, and the next time will be easier.

Since you're focused on Airbnb arbitrage and house hacking, you may want to start with markets where short-term rentals are allowed and don't have too many significant barriers to entry. Several areas either don't allow it or require a permitting/licensing process, so make sure to do your research on that aspect before you move forward. Also, when looking at house hacks, duplexes or triplexes can give you a great mix of cash flow and lower living expenses. Keep it simple, keep learning by doing, and take things one step at a time. Best of luck to you!
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- Chris Cline
  OP
  Investor · Bandon, OR · Member since 2025 · 4 posts · 6 votes
  1y
  @Troy Christiansen Thank you for your response, suggestions and encouragement. I will certainly heed your advice.
  1 Reply
Wale LawalBusiness Member
Real Estate Broker · Houston | Dallas | Austin, TX · Member since 2018 · 5k+ posts · 2k+ votes
1y
@Chris Cline
It’s great that you’ve been actively researching and underwriting properties—taking action is key to overcoming analysis paralysis. Since financial decisions feel challenging, focus on simplifying your criteria (cash flow, demand, and risk tolerance) and set a deadline to make your first move. Start small, trust your research, and take the leap—real growth comes from experience!
Good luck!
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- Chris Cline
  OP
  Investor · Bandon, OR · Member since 2025 · 4 posts · 6 votes
  1y
  @Wale Lawal Thank you for your response, advice and encouragement!
  1 Reply
Christopher Pride
Real Estate Consultant · Brookings, OR · Member since 2018 · 43 posts · 20 votes
1y
Hi Chris, aside from clearly having an intelligent name, we're neighbors! It looks like we're both currently looking in the same markets for a good deal. Perhaps we should discuss. I will happily share what I know.
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- Chris Cline
  OP
  Investor · Bandon, OR · Member since 2025 · 4 posts · 6 votes
  1y
  @Christopher Pride Hey, Christopher! Thanks for reaching out. I am absolutely open to discussing markets we're both looking at.
  1 Reply
Min ZhangBusiness Member
Real Estate Agent · Member since 2022 · 1k+ posts · 1k+ votes
1y
Hey Chris! With STRs, I'd recommend diving into one market at a time. There's a lot of data out there, but too much can be paralyzing. Start with the basics: market demand, average nightly rates, occupancy rates, and local regulations. Some markets are more STR-friendly than others, so make sure you research city ordinances to avoid any surprises. It's also important to factor in all costs beyond just the rent. Items like utilities, cleaning fees, insurance, and platform fees can add up. A lot of people make the mistake of only focusing on the potential income and forgetting about the operational side of managing an STR.

For LTR, I’d suggest focusing more on narrowing down your criteria. Instead of trying to analyze every potential deal to perfection, set a specific goal and narrow your search to just a few markets that meet that criteria. Since you've been researching LTRs, I'd recommend continuing to build a strong foundation with those and then considering short-term rentals once you're comfortable. You can use rentometer or zillow to estimate potential market rent to get started. Best of luck on your search!
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