Hey Chad,
I am a commercial real estate attorney in the Detroit area with some small investments on the side (please note that none of this is legal advice and shouldn't be taken as such). I am just getting started in my career as an attorney (I've been practicing for three years) and investor, but I have worked on hundreds of large deals. Many of those deals involve the acquisition, financing (CMBS loans, usually) and disposition of large apartment complexes located throughout the country. I do not think that your ultimate goal is too lofty, but I do think that you should probably gain a good track record and learn as much as you can first. You will need access to money - not just bank financing, but private equity, as well. In order to do that, you will need experience. Obviously each deal is different and there are different requirements depending on the size, but I think you guys have it right. Learn as much as you can. Keep acquiring 2-4 unit properties (5+ units qualifies as commercial, as I'm sure you already know). Grow your cash flow and continue to save money for bigger and bigger deals. Our clients are generally moderately to very sophisticated. They have been in the real estate world for years, starting as either a second generation developer/investor or beginning their careers as attorneys, accountants, brokers, agents, etc. Obviously that doesn't apply to everyone, though. Some certainly start from nothing and create a career simply from real estate investing.
As far as leaving your day job in IT for a day job in real estate, only you can make that decision. It depends many factors, such as your seniority and pay in your IT job versus where you would have to start in real estate. You may have a very solid salary that you wouldn't be able to obtain right off the bat in real estate. It would probably take you some time to really start making some more money in a real estate day job. For example, you would need to be a real estate salesperson for at least three years before you can take the broker's test. The people that I deal with day to day are developers/investors (some of which are institutional, but many of which are private major players - I mention this because you can certainly pursue working for a developer in some capacity), title companies, property managers, brokers, real estate agents, leasing agents, mortgage brokers/loan officers, large tenants' real estate departments and many city officials/workers. It totally depends on what you want to do. The title people I know are, in my opinion, the most immersed in the community (meaning they have the most real estate connections) due to the nature of what they do; however, they don't necessarily get much experience on the business or mechanical side of the transaction. Brokers and agents closely follow the transaction from start to finish (if they're worth their salt), so they get a very good idea of the acquisition, sales and leasing aspects; however, they are not involved with day to day activities. They are generally gone once the transaction has ended. Mortgage brokers and loan officers, if they're good, can get to know many people in the industry and learn a ton about financing. These are just a few examples that don't require extra schooling (although many title people are lawyers and certain other certifications may be required for the other examples). It really just depends on what you want to accomplish with a RE day job and what you think you would enjoy. Plus, you're young so you have time to switch careers!
The bottom line is that I don't think you are taking the easy way out. I think it's smart. You will build your RE knowledge brick by brick (no RE pun intended) while continuing to grow your own portfolio. These are just my opinions from my short experience, so take it for what it is. Feel free to reach out to speak further and good luck!
