Tenants in many markets already believe they pay too much (contrary to recent studies that show rent to property values have never been lower for the large US cities).If my insurance costs are not double my current rates over the next couple years, I will be pleasantly surprised.  

One strategy is to pursue properties (in your preferred markets) that have been listed for sale for over 90 days (even longer is better).

Fairmont is a good little market!

They offer weekly training sessions on everything from investing and construction to vendor management, cash management, market analysis, and home underwriting.

I was studying the market and my rent will be just enough to cover the mortgage and HOA fee now I might to pay out of pocket for insurance but don't want to sell it yet because the area is growing and might have good appreciation in the years that follow.

So overall experience of your QI to work in a number of markets and locations is really the key. 

As you embark on this journey, you'll learn the importance of market research, the art of negotiation, and the power of leveraging assets.

These numbers suggest this could be a strong buy-and-hold investment, assuming the market supports your rent and expense estimates.Good luck!

My go-to response is always: Do you have a Move-In Inspection to document the home's condition beforehand?

It’s exciting to hear about your plans to dive into this field, and Chicago is a fantastic market to explore once you move there.It sounds like you’re on the right track with your interest in House Hacking, Mid-Term Rentals, Short-Term Rentals, and the BRRRR strategy.