So, taking the money out to deploy it with the goal to make LESSer returns hardly sounds good. 

It can take a year or more to complete an ADU.

While you are not required to have a property manager for your long-term rental (short term is a different story), you can only handle administrative functions such as making phone calls, paying bills, selecting a contractor, etc. and must be completely hands off. 

We walked a model where it was nearly completed and the original buyer had decided to walk away, so the home was put back on the market at a $15,000 discount of the original list/contract price. 

@Russell Thomas Sounds a great position to be in.

I make a little over 100k a year and have 50k currently ready for a down payment. any insight would be helpful.Hey Brandon, totally can relate with you being from an expensive real estate market - I moved to Columbus a few years ago (from Portland, Oregon which was super expensive) to become a full time real estate investor, and ever since, I've completed quite a lot of BRRRRs, flips, and own a successful rental portfolio here in Columbus Ohio.

Recently, I completed a short-term rental (STR) training program and I am eager to explore more opportunities in this field.

Renting out camping areas on your wooded piece of land sounds like an interesting idea!

Directly North is still A market-Shawnee)It looks good with straight investor metrics using Fannie Mae conforming loans (25% down, 7.1% rate with a few points) and easy ARV monthly rent of $1700/unit ( I get this number based on the exact same floor plan in Raytown with complete rehab placing a tenant at $1500, and Raytown gets lower rents than Roeland Park KS.)

Without trying to sound like a dating website, I’d love to connect with like minded people on their thoughts and views of the industry and different markets - either in Chicago or elsewhere.