As a broker, you’ve already got a strong foundation, which will give you an edge in finding and structuring great deals.Since you're in Chicago, have you considered house hacking as a starting point?

Good Morning - My realtor came to me with an offer for an FHA loan but they want to move in this weekend.  

My contractor brought me a house off the market.

If it's the case that you are in an area where this is a consistent problem, it may be better to install a whole house surge protector at the main panel.

There is an affordable housing crisis here in America.

As you progress your bookkeeping business, you'll likely want to learn how to export statements from a variety of property management platforms, as investor books are housed in bank accounts, spreadsheets, and a variety of property management and accounting software!

I have seen a few people mention that house hacking is possible as well but tricky to find a property that can support that approach.

If heating expense is part of your consideration, I would look at the house's insulation, windows etc.

I kept thinking it would get easier and less nervy as I bought more houses.

It's growing rapidly and price of labor/ housing is dirt cheap.