But one problem, at this age I have disadvantages.

The RLTO already puts landlords at a disadvantage, adding this to the mix would be disastrous for the commercial market in Chicago. 

Go over the advantages and disadvantages and let them make the decision.Do NOT tell them you will buy their house and let them think they are finally having their house sold.Big Mistake.There is a system to go about it and it works every time.

Even though there's all these great advantages, there definitely is a few disadvantages. 

You have a disadvantage because, just by being licensed, you're open to being investigated by the RE commission in your state, and you have more legal requirements than a normal investor, and more leverage against you in court if you ever get sued. 

Adding PR as a state would mean many financial disadvantages to the US as opposed to the current "limbo status" of "belong to the US but not part of it".

I know that getting something expunged in Virginia is extremely difficult.It's always great to start out in your own back yard and of course you could find an agent to partner with or get into wholesaling, etc.I'm in DC and we have the advantage (or serious disadvantage) of being able to work in 3 different states with 3 different jurisdictions at the same time.

This is a disadvantage to arbitrage.

At the same time I think both private and public have their advantages and disadvantages and neither is 100% superior to the other.

If you want to be successful at RE you will be at a severe disadvantage if you quit school and let me tell you breaking into this business is already hard to do .