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Jaylen Jones
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First time investor looking for Multi unit properties.

Jaylen Jones
Posted Jan 12 2023, 06:58

Good morning everyone,

I am a first time investor in the Chicago area looking to find a muli unit property and fill it up with some tenants. I am 22 years old and I drive trucks for a living right now. I want to get my first property under my belt within the first 6 months of this year and create a positive cash flow to re invest my money. I have the skills of hard work, consistency, and dedication to something that I am involved in and this is something I plan on doing for a very long time. Any advice will help me at the moment and will be greatly appreciated. Thank you for your time!  

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Zac Gronda
  • Real Estate Agent
  • Knoxville, TN
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Zac Gronda
  • Real Estate Agent
  • Knoxville, TN
Replied Jan 12 2023, 07:37

I started with single family units and then duplex units.  If your looking for cash flow, look for the deal on the front end if possible, with tenets already included in the deal that make its flow, considering your on the road you need to make sure they are good tenants prior to investing and the property does not need a lot of investment in the structure.   

Also if your out of town a lot i would find a reliable property manager or a friend that can pretend to be one until you get off the ground.  


lastly get a good loan locked in and save for a bigger down payment so you don't get crushed by the interest rates we are experiencing right now 

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Bob Stevens
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#3 General Landlording & Rental Properties Contributor
  • Real Estate Consultant
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Bob Stevens
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  • Real Estate Consultant
  • Cleveland
Replied Jan 12 2023, 08:04
Quote from @Jaylen Jones:

Good morning everyone,

I am a first time investor in the Chicago area looking to find a muli unit property and fill it up with some tenants. I am 22 years old and I drive trucks for a living right now. I want to get my first property under my belt within the first 6 months of this year and create a positive cash flow to re invest my money. I have the skills of hard work, consistency, and dedication to something that I am involved in and this is something I plan on doing for a very long time. Any advice will help me at the moment and will be greatly appreciated. Thank you for your time!  

 YES STOP!! 1ST connect with someone doing deals, LEARN then apply what you learn, Do NOT just try and go it alone, it will not end well. You do not know what to pay, ( do you have 50 60 70 k ? )  how much reno will cost, how to get tenants etc, even know how to figure out your net cap ?  LEARN 1ST 

All the best 

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Paul De Luca
  • Real Estate Agent
  • Chicago, IL
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Paul De Luca
  • Real Estate Agent
  • Chicago, IL
Replied Jan 12 2023, 08:19
Quote from @Jaylen Jones:

Good morning everyone,

I am a first time investor in the Chicago area looking to find a muli unit property and fill it up with some tenants. I am 22 years old and I drive trucks for a living right now. I want to get my first property under my belt within the first 6 months of this year and create a positive cash flow to re invest my money. I have the skills of hard work, consistency, and dedication to something that I am involved in and this is something I plan on doing for a very long time. Any advice will help me at the moment and will be greatly appreciated. Thank you for your time!  


 I highly recommend house hacking not only your first 2-4 unit property, but as many times as you can (especially in your 20s). That way you can get your first property with minimal out of pocket expense (low down payment), rent out the other units, gain experience as a landlord, move out after a year and then rinse & repeat.

  • Real Estate Agent Illinois (#475.190985)

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Jaylen Jones
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Jaylen Jones
Replied Jan 12 2023, 10:54
Quote from @Paul De Luca:
Quote from @Jaylen Jones:

Good morning everyone,

I am a first time investor in the Chicago area looking to find a muli unit property and fill it up with some tenants. I am 22 years old and I drive trucks for a living right now. I want to get my first property under my belt within the first 6 months of this year and create a positive cash flow to re invest my money. I have the skills of hard work, consistency, and dedication to something that I am involved in and this is something I plan on doing for a very long time. Any advice will help me at the moment and will be greatly appreciated. Thank you for your time!  


 I highly recommend house hacking not only your first 2-4 unit property, but as many times as you can (especially in your 20s). That way you can get your first property with minimal out of pocket expense (low down payment), rent out the other units, gain experience as a landlord, move out after a year and then rinse & repeat.

What is house hacking ? 

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Steven Foster Wilson
  • Rental Property Investor
  • Columbus, OH
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Steven Foster Wilson
  • Rental Property Investor
  • Columbus, OH
Replied Jan 12 2023, 11:03
Quote from @Jaylen Jones:
Quote from @Paul De Luca:
Quote from @Jaylen Jones:

Good morning everyone,

I am a first time investor in the Chicago area looking to find a muli unit property and fill it up with some tenants. I am 22 years old and I drive trucks for a living right now. I want to get my first property under my belt within the first 6 months of this year and create a positive cash flow to re invest my money. I have the skills of hard work, consistency, and dedication to something that I am involved in and this is something I plan on doing for a very long time. Any advice will help me at the moment and will be greatly appreciated. Thank you for your time!  


 I highly recommend house hacking not only your first 2-4 unit property, but as many times as you can (especially in your 20s). That way you can get your first property with minimal out of pocket expense (low down payment), rent out the other units, gain experience as a landlord, move out after a year and then rinse & repeat.

What is house hacking ? 

Hey Jaylen, House hacking means finding a way to generate income from your current home. Traditionally, this is meant for multifamily homes. It's basically you living on a multi unit while having to have your tenants pay your mortgage. You get to build equity while maintaining the property doing this. You can learn more about it here: 

https://www.biggerpockets.com/...

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Paul De Luca
  • Real Estate Agent
  • Chicago, IL
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Paul De Luca
  • Real Estate Agent
  • Chicago, IL
Replied Jan 12 2023, 11:04
Quote from @Jaylen Jones:
Quote from @Paul De Luca:
Quote from @Jaylen Jones:

Good morning everyone,

I am a first time investor in the Chicago area looking to find a muli unit property and fill it up with some tenants. I am 22 years old and I drive trucks for a living right now. I want to get my first property under my belt within the first 6 months of this year and create a positive cash flow to re invest my money. I have the skills of hard work, consistency, and dedication to something that I am involved in and this is something I plan on doing for a very long time. Any advice will help me at the moment and will be greatly appreciated. Thank you for your time!  


 I highly recommend house hacking not only your first 2-4 unit property, but as many times as you can (especially in your 20s). That way you can get your first property with minimal out of pocket expense (low down payment), rent out the other units, gain experience as a landlord, move out after a year and then rinse & repeat.

What is house hacking ? 

 Typically it means buying a 2-4 unit property, living in one unit, and renting out the other units. Some people house hack single family homes or condos by living in one bedroom and renting out the other rooms.

  • Real Estate Agent Illinois (#475.190985)

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Jaylen Jones
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Jaylen Jones
Replied Jan 12 2023, 11:04
Quote from @Steven Foster Wilson:
Quote from @Jaylen Jones:
Quote from @Paul De Luca:
Quote from @Jaylen Jones:

Good morning everyone,

I am a first time investor in the Chicago area looking to find a muli unit property and fill it up with some tenants. I am 22 years old and I drive trucks for a living right now. I want to get my first property under my belt within the first 6 months of this year and create a positive cash flow to re invest my money. I have the skills of hard work, consistency, and dedication to something that I am involved in and this is something I plan on doing for a very long time. Any advice will help me at the moment and will be greatly appreciated. Thank you for your time!  


 I highly recommend house hacking not only your first 2-4 unit property, but as many times as you can (especially in your 20s). That way you can get your first property with minimal out of pocket expense (low down payment), rent out the other units, gain experience as a landlord, move out after a year and then rinse & repeat.

What is house hacking ? 

Hey Jaylen, House hacking means finding a way to generate income from your current home. Traditionally, this is meant for multifamily homes. It's basically you living on a multi unit while having to have your tenants pay your mortgage. You get to build equity while maintaining the property doing this. You can learn more about it here: 

https://www.biggerpockets.com/...

Okay, I’ll look into that Much appreciated! 

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John Warren
  • Real Estate Broker
  • 1658 N. Milwaukee Ave Ste B PMP 18969 Chicago, IL 60647
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John Warren
  • Real Estate Broker
  • 1658 N. Milwaukee Ave Ste B PMP 18969 Chicago, IL 60647
Replied Jan 12 2023, 14:10

@Jaylen Jones the first step should always be talking to a lender. I personally work with @Joshua Jones for all of my residential loans, and he is the best in the business. I think it is awesome that you are looking to start young at only 22, and I am sure you will be successful with that mindset! 

  • Real Estate Agent IL (#475.166619)

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Joshua Jones
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Joshua Jones
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Replied Jan 12 2023, 17:57

Thank you @John Warren. @Jaylen Jones when it comes to multi units, you have a few options. There are FHA mortgages, conventional mortgages and renovation mortgages if you find a place that has good bones but needs some work. Getting a great team together to help you grow is key. Feel free to private message me if you have lending questions or about the team I work with for this process. I bought my first place when I was 21 so I have a passion for young investors and understand what you are looking to do.

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Jaylen Jones
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Jaylen Jones
Replied Jan 13 2023, 04:10
Quote from @John Warren:

@Jaylen Jones the first step should always be talking to a lender. I personally work with @Joshua Jones for all of my residential loans, and he is the best in the business. I think it is awesome that you are looking to start young at only 22, and I am sure you will be successful with that mindset! 


 Thank you for the help and connection.

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Jaylen Jones
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Jaylen Jones
Replied Jan 13 2023, 04:12
Quote from @Joshua Jones:

Thank you @John Warren. @Jaylen Jones when it comes to multi units, you have a few options. There are FHA mortgages, conventional mortgages and renovation mortgages if you find a place that has good bones but needs some work. Getting a great team together to help you grow is key. Feel free to private message me if you have lending questions or about the team I work with for this process. I bought my first place when I was 21 so I have a passion for young investors and understand what you are looking to do.

Okay, I will be reaching out. Appreciate the information looking forward to speaking more about it.

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Alex Talcott
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Alex Talcott
  • Attorney
  • Durham, NH
Replied Jan 13 2023, 05:26

Do you drive trucks around the city or interstate?

Either way, out of state is likely easier for cash flow -- and enough cash flow and timely exits that allow for reinvestment in other property deals. You may be able to save your noble hard work, consistency, and dedication for other aspects of your life.

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Crystal Smith
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Crystal Smith
  • Real Estate Broker
  • Chicago, IL
ModeratorReplied Jan 13 2023, 11:04
Quote from @Jaylen Jones:

Good morning everyone,

I am a first time investor in the Chicago area looking to find a muli unit property and fill it up with some tenants. I am 22 years old and I drive trucks for a living right now. I want to get my first property under my belt within the first 6 months of this year and create a positive cash flow to re invest my money. I have the skills of hard work, consistency, and dedication to something that I am involved in and this is something I plan on doing for a very long time. Any advice will help me at the moment and will be greatly appreciated. Thank you for your time!  



My advice is below:

1. Decide if you want to live in your first investment with tenants or if you want a pure investment. 

2. If you're comfortable with living in the investment then start researching and interviewing lenders to see what kind of low downpayment owner-occupied loan you may qualify. If you do not want to live in the investment then see what kind of non-owner occupied loan you may qualify for.   If you find that you won't qualify for a loan  then build a plan so you'll eventually qualify

3. While doing number 2 you should also learn how much cash you'll need to execute your plan. Downpayment, Cash for closing, cash for reserves,...... 

4. The business is about leveraging or using Other People's money (OPM) to grow your business. Do not approach people to borrow money at this point but everyone you meet while doing your job as a truck driver could potentially be an investor.  And at the age of 22 you're going to meet a lot of people. Create a database of those people.  And then at the right time reach out to them

5. Purchase Robert Kiyosaki's book Rich Dad Poor Dad; then look for local Cash Flow Games to participate in

I could extend the list to 100 but I think this is a good place for you to start.

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Mark Ainley
Property Manager
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Mark Ainley
Property Manager
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  • Property Manager
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Replied Jan 13 2023, 12:55


@Jaylen Jones  Great to hear your drive(No pun intended) and love to hear the aggressive timeline.  What area of the Chicago Metro you looking at?

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Jaylen Jones
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Jaylen Jones
Replied Jan 13 2023, 15:32
Quote from @Crystal Smith:
Quote from @Jaylen Jones:

Good morning everyone,

I am a first time investor in the Chicago area looking to find a muli unit property and fill it up with some tenants. I am 22 years old and I drive trucks for a living right now. I want to get my first property under my belt within the first 6 months of this year and create a positive cash flow to re invest my money. I have the skills of hard work, consistency, and dedication to something that I am involved in and this is something I plan on doing for a very long time. Any advice will help me at the moment and will be greatly appreciated. Thank you for your time!  



My advice is below:

1. Decide if you want to live in your first investment with tenants or if you want a pure investment. 

2. If you're comfortable with living in the investment then start researching and interviewing lenders to see what kind of low downpayment owner-occupied loan you may qualify. If you do not want to live in the investment then see what kind of non-owner occupied loan you may qualify for.   If you find that you won't qualify for a loan  then build a plan so you'll eventually qualify

3. While doing number 2 you should also learn how much cash you'll need to execute your plan. Downpayment, Cash for closing, cash for reserves,...... 

4. The business is about leveraging or using Other People's money (OPM) to grow your business. Do not approach people to borrow money at this point but everyone you meet while doing your job as a truck driver could potentially be an investor.  And at the age of 22 you're going to meet a lot of people. Create a database of those people.  And then at the right time reach out to them

5. Purchase Robert Kiyosaki's book Rich Dad Poor Dad; then look for local Cash Flow Games to participate in

I could extend the list to 100 but I think this is a good place for you to start.

thank you for the great advise!

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Sam McCormack
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Sam McCormack
  • Real Estate Agent
  • Cincinnati, OH
Replied Jan 14 2023, 08:50

@Jaylen Jones

Hi Jaylen, do you plan to stay investing where you are located? Or OOS? If you are looking OOS, I know Greater Cincinnati could have what you are looking for! There are small multifamily deals to be done that you may love. Let me know if you are interested in this cash flowing market!

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Jonathan Klemm
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Jonathan Klemm
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ModeratorReplied Jan 16 2023, 08:11

Hey @Jaylen Jones -  Congrats on getting on the real estate train so early! You will go a long way with hard work, consistency, and dedication!  

For me the biggest attribute that changed my life was self-awareness....consider listening to some Ed Mylett podcasts while you are driving, he is great.  I took a different approach than most, in the fact that most people spend 80% of their time on real estate and 20% on self-improvement......I spent 80% on self-improvement and only 20% on real estate, which has been the best choice of my life.  For me if you follow these 3 steps you will be successful in whatever you do.

1.  Educate/read/listen

2.  Network

3.  Take action/Be decisive

I am also in Chicago so happy to connect to talk real estate or life anytime.