All Forum Posts by: Shamar Gregg

Matthew,

I’d also suggest adding Chicago to the list. The city's appreciation, vacancy rate, cap rates are truly unparalleled when compared to the other markets you’ve mentioned. I have a strong team on the ground for any type of value add. I’d love to connect and discuss the numbers further.

@Greg P.

I primarily focus on real estate investments in Chicago, working with out-of-state investors who want to tap into the local market from afar. I also help investors analyze deals in any state, providing insights to ensure they make informed decisions.

While the markets Greg mentioned are excellent for investing and tend to be more landlord-friendly, Chicago—being the third-largest city in the U.S.—offers unique advantages. The rental demand here is consistently strong, so vacancies are rare and turnover is quick. This isn’t always the case in more sparsely populated areas, where vacancy periods can be longer, affecting cash flow. In contrast, Chicago’s prime location drives higher rental rates compared to many other cities in the Midwest, which can significantly impact your return on investment. Looking forward to connecting. 

Personally, I started my investment journey with multifamily properties before moving into single-family homes. I recommend starting with multifamily if you're just getting started with limited capital. For example, I used an FHA loan (3.5% down) to purchase a 4-unit property, which allowed me to put down a low deposit while still generating strong cash flow from multiple rental units. Same can be done with VA loans and Conventional 5%.

Multifamily properties provide the advantage of multiple income streams, which can help offset vacancies and reduce risk. However, once I transitioned into single-family homes, I realized that the cash flow difference wasn’t as significant, but the management became simpler. With a single-family, you have one property, which means fewer moving parts.

If you have the funds to scale, I would recommend moving toward single-family homes, but if you're just starting out, multifamily can be a smarter choice. It’s the "bigger bird, smaller stone" approach: multifamily offers more immediate cash flow and flexibility when you're getting started, while single-family homes can provide more simplicity and scalability once you've built up some capital.

@Greg P.

With a $750K budget, I recommend focusing on single-family home investments in the Midwest. This region offers attractive home prices in the $100K–$200K range, combined with rental yields that often exceed the 1% rule. This provides an excellent opportunity to purchase properties, make light renovations to increase both rental income and property value, and optimize cash flow. Especially in a region where homes often have great bones but need interior TLC. 

From there, work with a reliable cash-out refinance partner to continually access your equity, allowing you to keep non-taxable cash on hand for future investments. By repeating this process, you can scale your portfolio while working toward your desired monthly income goals. This strategy offers both stability and growth potential, especially if you're able to identify high-demand rental area. For example, in market I see single homes valued 100-150K, taxes 1-4K, rents 1800-2200.

Hey @Jonathan Klemm, thank you!

1. I purchased the property this past october. 

2. I am sitting on it yes because I am currently in the process of finishing up my 3 unit. 

3. I found the deal through the MLS but I was able to negotiate it down because this was an estate sale.

4. I am either going to fund through a hardmoney or myself. 

5. The is considered Chatham, its off the express way by 87th.   

Investment Info:

Single-family residence buy & hold investment in Chicago.

Purchase price: $60,000

Purchase this property for my first BRRRR. I've done a few multifamily deals before but I bought this property because of its BRRRR potential. Fell in love with it because it hit all my boxes. Next to a tennis court, basement space for additional square footage to increase value, currently in live-able condition, multiple comparables. I had a professional appraisal done it in August 2023 and it came back at 230K. As of December, there is a house a block (0.19 miles)over going for 255K!

What made you interested in investing in this type of deal?

ARV potential and potential rent for 5 bedrooms for the area. Looking to get this started once I complete my 3 unit renovations.

How did you add value to the deal?

Adding two bedrooms in basement plus bathroom. Making it into a 5 Bed/ 2 Bath.

@Tom O. 

I have a good connect with an insurance broker at state farm here in Chicago. I just referred a client of mine for his three unit and his quote was under $1700 for the year. Obviously I can't comment on the price you'd get for a 4 unit but I would be happy to refer you to her if you'd like to explore that option. 

 Hi Angelo, 

Definitely could impart some advice here. I used an FHA loan to purchase a 4 unit and lived in one of the units. Currently doing a FHA 203K now as well.

1. The process works just like a regular home purchase. Your first step is getting pre-approved through a lender. Your lender will guide you as far as what price points you should be looking at based on your credit rating, income, etc. I have lenders who perform soft credit checks at first if you need a lender connect. 

2. You'll obviously then go search for something that fits into that range from your lender. Once you find the property, your lender should be able to run the numbers using hypothetical numbers based on the comparables rent. Your realtor then places the offer and if everything goes well, you're under contract! 

3. In part 2, I stated hypothetical because your rental information actually comes from the appraiser once you're under contract. For 3 and 4 units through FHA, your mortgage cannot be more than 75 percent of total rents. Therefore, make sure your realtor is using good comparables before you go under contract. I've seen deals fall through because the estimated numbers were way to high and the appraisal never supported those rents.

4. My experience was great. Of course its challenging being a landlord but my overall personal experience was great. I ended up selling two years later to cash out and reinvest in more! 

I have realtor connects in all 50 states if you need someone. This way I could tag along your journey and answer anymore questions you may have! 

 Thank you! 

Small multi-family (2-4 units) buy & hold investment.

Purchase price: $230,000
Cash invested: $260,000

This property is my second investment. It is a 3 unit with a 203K rehab on it. Currently in the process of waiting on permits from the city. Building as is 9 bed/ 3 bath, 1500 sq each unit. Currently the plans are to convert the dinning room into a master bedroom with a bathroom. Purchase $230K (17K seller credit) so technically i paid $217K! 260K renno budget. Estimated completion end of year.

ARV 505K