Introduction & Real Estate Licensing Question

[Mary Arents]

Hello BP Community!

I live in Chicago and have had an interest in real estate for many years.

Four years ago, my spouse and I purchased a three-flat in the Lincoln Square neighborhood, moved in, rented the other two units out, eventually converted the property to condos, sold the other two units to friends, and now own our condo outright. The primary motivators for this project were (1) a dream to create a shared living community; and (2) to live within our means. We are fortunate to have amazing neighbors and zero debt!

After all of this, my interest in real estate remains, and I'd like to do more in the field. I am exploring both becoming a real estate broker and real estate investing.

Questions I have right now about becoming a real estate broker:

(1) What real estate pre-licensing programs can you recommend - especially for online coursework? And why?

(2) What brokerages can you recommend for someone like me who would like to get into real estate investing eventually? And why?

Question I have right now about becoming a real estate investor:

(1) For those with experience with small multi-family property investments in Chicago, how did you get your start? I'd love to hear some examples. The small multi-family properties in my area seem best (financially) for house hacking, but I'm not sure if/when we will be willing to move.

For reference, my goals are to net >$100K annually within 3-5 years from brokerage and investing while also setting the stage for early retirement. I'm 39 now. I am currently employed full-time but not wanting to stay in my current job long-term.

I welcome input from those who are farther down the road! Also open to local meet-ups to learn more from experienced folks in my area. Thank you!