New Investor from Chicago, IL

[Steve Henry]

Hello BiggerPockets Community!

My name is Steve Henry and I am a new investor from the Chicagoland area.  I've lived in this area my whole life and I'm looking to get started generating cash flow from rental properties.  Like many of you, I turned to the internet and stumbled upon this great resource known as BiggerPockets. I have some experience in property management and leasing, but would like to purchase a multifamily property and see where it goes from there.  I plan on focusing on buy and hold properties in the beginning but will consider other types of investments.  Some of my hobbies include sports, traveling, music and enjoying time with family and friends. 

A few questions for other investors on the site:

How did you find your first deal?

What is the biggest struggle you faced when you were a new investor?

How did you overcome that struggle?

What are some books that you'd recommend for new investors?

Thanks!

[Jason Marcordes]

Hi Steve!

Welcome to BP and the world of REI. I'm a fellow investor and own a property management firm in the Chicagoland area.

- My first deal I found on the MLS about 7 years ago. I was already in property management and helping other people build their portfolio so I finally decided to buy a property for myself. I looked at over 100 properties before I settled on a single family home in Dolton for $35,000. It was move in ready and cash flowed like a beast. I sold it late last year for $87,500. I wish I would've bought 100 of those lol.

- My biggest struggle has always been finding quality contractors at a reasonable price. I've used a ton of different crews and it's tough to find quality people. I just recently started doing gut rehabs in the city and dealing with the City of Chicago/Permits/Inspections has also been tough. I would highly recommend sticking with contractors that have been referred to you by someone you know or someone on BP that has actually used the contractor. Also, get EVERYTHING in writing.

- Books: I love to read but IMO there is no one book that's going to teach you the secret to REI. I found myself reading and reading and reading before I told myself I'm never going to learn unless I pull the trigger. Of course I highly recommend reading but don't get caught in the paralysis by analysis trap and think that you need to keep learning before you buy your first deal. I would find a good solid and safe deal (doesn't have to be a home run) at a low entry point and jump in. With that being said, you asked so....Rich Dad, Poor Dad, Millionaire Real Estate Investor, and Nothing Down for the 2000s (gets you thinking creatively about deals). There's a ton of great books out there though.

Good luck on your journey! If you ever need anything, feel free to reach out.

Take Care.