It’s a market where cash flow is achievable without needing a massive upfront investment.

Any marketing should always be based on the information provided by sellers in a deal. 

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.

Quote from @Kevin Hintz: I can totally relate to the tight market and how hard it is to find deals.

Instead of following trends, tailor your space to the lifestyle of your target market.

I dont believe so but am not an expert on the topic - I do know that in Texas at least, it is marketed for owner occupants first and then after a certain time period they allow investors to put offers in. 

STR seems to have better tax benefits (in the right market) but is it worth it at a distance ???

Study the market.

If things go sideways, you discovery greater rehab expenses, the market takes a turn for the worse, you can get in the red quickly. 

Charge market rent.