Real estate investing has been a passion of mine for time with my mother also having invested early on where I likely have gotten the love and desire to follow similar foot steps.I have taken last 6 months to educate myself and currently own a single family home as primary residence and would like to expand to multi family properties (2-4 units) for additional stream of income, not to mention potential tax benefits for long-term investing.Based on current living situation, I have a fair amount of equity established in my primary residency along with having enough cash to either pay off house completely or use towards investing in a multi family property.Given that I'm the sole source of income for our household with my wife being the home maker for our two kids under 2, trying to weigh out risks with getting started now or perhaps waiting. 

Knowing your long-term plans can help you build a long-term financing strategy so that you are not just worried about purchase number 4, but also purchases 5 - 20+ (if you plan to continue to invest).I'm an investor and licensed mortgage broker.

Hi @Evan Coopersmith, I'm an investor and licensed mortgage broker here in Chicago (Oak Park).

If you are going to use a mortgage originator, make sure they kiss the deal with their license number.

This contractor has 0 reviews on yelp which I found a bit sketchy, but was able to vet him by his contractor's license, worker's comp, and by visiting some of his ongoing projects.

Needless to say, many parties are involved, and they all need to be established and verified, or your business will suffer greatly. 

Or does one need a special license / need to open a company?   

Also, you don’t need a business license just to look at properties, but if you buy a bigger property, like a multi-family unit, you might need a certificate of occupancy, depending on the local rules.For business trips, most expenses can be deductible, but if it’s part personal and part business, you can only deduct the business portion.

I have never done this before even though I am a licensed real estate managing broker however I don't feel confident enough.

When it's a well established company like Apple, they aren't likely to be going out of business so there is some certainty that there will be in increase in demand for quite some time.