Multi unit or single family strategy

[Ryan Green]

All,

I am new to Bigger Pockets and am really excited to become part of the community. I have  a question I would love advice on. Ill give you a high level overview of the situation and my goals.

My overall goal is to buy and hold rental properties and create 200k+ cash flow / year over the next 10 years. I am a licensed agent, have done a few flips and  I currently own 5 properties that net about 25k per year. I have a strong amount of cash available to buy a larger commercial multi unit. However, I haven't had much success finding a great deal in my current Chicago market. I have read and researched several different strategies and I am going back and forth on 3 strategies and I would feedback/advice. Below are the 3 strategies:

1. Be patient, keep saving money and keep focused on buying a larger multi unit when something comes up in my Chicago market. The larger multi unit will be in the 1-1.5 mill range. It may have a cap around 8% based off my market. I'm a licensed residential agent but don't have much experience in the commercial space. I am also willing to partner with a commercial agent to take over and help find me a deal. I've tried with no luck yet.

2. Buy 2-3 single family/condos at 80% to value in the 100k range, put some work into for instant equity and rent out at about 500 net profit a month. Refinance and repeat over the next 10+ years. I'm a licensed agent so this option is easier for me to find properties, less competitive (I'm not a full time investor), and I am personally more skilled at valuing these properties and acquiring them. However, this method will obviously take more time.

3. I've also even thought about purchasing a larger multi unit in another market (Currently in Chicago but I know areas in WI may be lower cost to get into and cash on cash returns are higher). There are drawbacks to this but also several pros. I would obviously need to really dive into and understand the market before jumping in.

I am extremely eager to keep growing my portfolio and would love to hear your thoughts! Thank you all in advance for the feedback!

Ryan