New Investors: Ask Me Anything

New Investors: Ask Me Anything

Jonathan GreeneBusiness Member
Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes

If you are just getting into real estate investing and have a question that you need an honest answer to, ask me anything here. But don't ask a question if you are hoping to get a certain answer, and don't ask a question that you can find an answer to in the forums 100 times because that won't help you.

My areas of expertise are off-market acquisition, flipping, short-term rentals, fix and live, landlording, on-market real estate and real estate teams, mindset, and how to build relationships in the business, among others. I was a guest on episode 584 of the BiggerPockets podcast so fire away.

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Residential Real Estate Broker · Sedona, AZ · Member since 2017 · 754 posts · 504 votes
4y
Quote from @Jonathan Greene:

If you are just getting into real estate investing and have a question that you need an honest answer to, ask me anything here. But don't ask a question if you are hoping to get a certain answer, and don't ask a question that you can find an answer to in the forums 100 times because that won't help you.

My areas of expertise are off-market acquisition, flipping, short-term rentals, fix and live, landlording, on-market real estate and real estate teams, mindset, and how to build relationships in the business, among others. I was a guest on episode 584 of the BiggerPockets podcast so fire away.


What is the airspeed of an unladen swallow?


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  • Member since 2022 · 25 posts · 8 votes
    4y

    I posted this as a new-member intro, so apologizing up front for the duplication.   

    I'm a 55yo retired military and soon-to-be-retired federal employee (14 more months!), considering one final encore career for 5-8 more years before fully retiring. Wondering if that is enough time to accumulate a portfolio of investment properties that will generate between $50k-$100k per year of income to (help) pay for may daughter's grad school (student loan debt is anathema to me), and then continue to augment our pension and stock portfolio throughout retirement and finally leave as inheritance. My only real estate experience is the four primary residences we've bought/sold for ourselves over the past 25+ years, one of which we tried to keep and rent, (but not a good experience). My research so far is leading me towards small multi-family properties as the most efficient path toward my goal.

    If I do pursue this, what is the best use of my time over this next year to educate and prepare? A real estate license? A BP boot camp? Can I start with the Multi-family Boot Camp, or does it build on the Rookie Boot Camp?

    Thank you!

    Brad

  • Jonathan GreeneBusiness Member
    OP
    Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes
    4y
    Quote from @Bradley R Stillabower:

    I posted this as a new-member intro, so apologizing up front for the duplication.   

    I'm a 55yo retired military and soon-to-be-retired federal employee (14 more months!), considering one final encore career for 5-8 more years before fully retiring. Wondering if that is enough time to accumulate a portfolio of investment properties that will generate between $50k-$100k per year of income to (help) pay for may daughter's grad school (student loan debt is anathema to me), and then continue to augment our pension and stock portfolio throughout retirement and finally leave as inheritance. My only real estate experience is the four primary residences we've bought/sold for ourselves over the past 25+ years, one of which we tried to keep and rent, (but not a good experience). My research so far is leading me towards small multi-family properties as the most efficient path toward my goal.

    If I do pursue this, what is the best use of my time over this next year to educate and prepare? A real estate license? A BP boot camp? Can I start with the Multi-family Boot Camp, or does it build on the Rookie Boot Camp?

    Thank you!

    Brad


     50-100k income from rental properties in 5-8 years is certainly doable, but it depends on what you are starting with (capital) and where you intend to plant your stakes. A real estate license would be of ancillary help in access, comps, and in my opinion is always worth the spend, but it's not the money maker unless you go real big. You would need some prep work before heading all into multifamily. Don't pay for courses, just learn and meet other investors to start.

  • Member since 2022 · 25 posts · 8 votes
    4y
    Quote from @Jonathan Greene:
    Quote from @Bradley R Stillabower:

    I posted this as a new-member intro, so apologizing up front for the duplication.   

    I'm a 55yo retired military and soon-to-be-retired federal employee (14 more months!), considering one final encore career for 5-8 more years before fully retiring. Wondering if that is enough time to accumulate a portfolio of investment properties that will generate between $50k-$100k per year of income to (help) pay for may daughter's grad school (student loan debt is anathema to me), and then continue to augment our pension and stock portfolio throughout retirement and finally leave as inheritance. My only real estate experience is the four primary residences we've bought/sold for ourselves over the past 25+ years, one of which we tried to keep and rent, (but not a good experience). My research so far is leading me towards small multi-family properties as the most efficient path toward my goal.

    If I do pursue this, what is the best use of my time over this next year to educate and prepare? A real estate license? A BP boot camp? Can I start with the Multi-family Boot Camp, or does it build on the Rookie Boot Camp?

    Thank you!

    Brad


     50-100k income from rental properties in 5-8 years is certainly doable, but it depends on what you are starting with (capital) and where you intend to plant your stakes. A real estate license would be of ancillary help in access, comps, and in my opinion is always worth the spend, but it's not the money maker unless you go real big. You would need some prep work before heading all into multifamily. Don't pay for courses, just learn and meet other investors to start.

    Thank you.  I'm still trying to understand the scope and scale of this business ("big" vs. small), but in a little over a year I will have access to make penalty-free withdrawals from my govt 401k (Thrift Savings Plan) and my initial thoughts are to tap into that for up to $100k to invest in 2-3 properties over that first year and assess how that starts getting me toward that annual income goal.   Between now and then I'll be trying to get educated on the processes, and researching where is the best market to get started.  How important is it stay local when starting out?
  • Real Estate Agent · Snohomish, WA · Member since 2020 · 99 posts · 49 votes
    4y

    Thank you Jonathan for the response. These didn’t even cross my mind, I’ll definitely be saving these.

  • Jonathan GreeneBusiness Member
    OP
    Real Estate Consultant · Madison, NJ · Member since 2016 · 6k+ posts · 7k+ votes
    4y
    Quote from @Bradley R Stillabower:
    Quote from @Jonathan Greene:
    Quote from @Bradley R Stillabower:

    I posted this as a new-member intro, so apologizing up front for the duplication.   

    I'm a 55yo retired military and soon-to-be-retired federal employee (14 more months!), considering one final encore career for 5-8 more years before fully retiring. Wondering if that is enough time to accumulate a portfolio of investment properties that will generate between $50k-$100k per year of income to (help) pay for may daughter's grad school (student loan debt is anathema to me), and then continue to augment our pension and stock portfolio throughout retirement and finally leave as inheritance. My only real estate experience is the four primary residences we've bought/sold for ourselves over the past 25+ years, one of which we tried to keep and rent, (but not a good experience). My research so far is leading me towards small multi-family properties as the most efficient path toward my goal.

    If I do pursue this, what is the best use of my time over this next year to educate and prepare? A real estate license? A BP boot camp? Can I start with the Multi-family Boot Camp, or does it build on the Rookie Boot Camp?

    Thank you!

    Brad


     50-100k income from rental properties in 5-8 years is certainly doable, but it depends on what you are starting with (capital) and where you intend to plant your stakes. A real estate license would be of ancillary help in access, comps, and in my opinion is always worth the spend, but it's not the money maker unless you go real big. You would need some prep work before heading all into multifamily. Don't pay for courses, just learn and meet other investors to start.

    Thank you.  I'm still trying to understand the scope and scale of this business ("big" vs. small), but in a little over a year I will have access to make penalty-free withdrawals from my govt 401k (Thrift Savings Plan) and my initial thoughts are to tap into that for up to $100k to invest in 2-3 properties over that first year and assess how that starts getting me toward that annual income goal.   Between now and then I'll be trying to get educated on the processes, and researching where is the best market to get started.  How important is it stay local when starting out?

    Personally, I think it is VERY important to stay quasi-local for your first couple of investments. Quasi-local to me is driveable without much hassle back and forth in a day, max 2 hours away. I don't think you can learn much if you invest OOS in turnkey to start or in a syndication. You want to learn hands-on.

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