Here’s a breakdown to help you navigate your first deal, incorporating advanced strategies, including 1031 exchanges, to attract a broader range of investors.Neighborhood Recommendations: Chicago offers a diverse range of neighborhoods for different investment goals:Wicker Park & West Town: These areas are known for their strong rental demand among young professionals and offer good potential for cash flow.Lake View: Ideal for attracting tenants who want to be close to downtown while enjoying local amenities.The Loop: A prime location for high-income renters, making it an attractive option if you’re planning to house hack and generate a steady stream of rental income.Property Types: Opt for properties that align with your investment goals.

Also pricing tends to be in the $250k+ range for SFHs, so cash flow may be difficult depending on how one is financing the deal.

If I had it to do again, I would press him for a range, but hindsight 20/20.

@Bob Asad, it is vastly easier to obtain a HELOC on an owner occupied residence than on a rental.  

What price range do you want to be in?  

@JD Martin the biggest issues have been related to furnaces, hot water, a missed clean, and broken hot tub. generous refunds have ranged from 25-100%, it really just depends on variables like nightly rate, guest demeanor, impact on their stay, etc. 

I was thinking the house would rent for 1200-1350 but it seems now the range is 1000-1200 with 1200 being the highest for the area so may be hard to get.

Many Of these properties are in the 1000-1400 Sqft range.

We have mostly 2-4 unit buildings compared to the larger stuff but that 5-50 range can be a good space to find deals in. 

The vast majority of lawsuits against Landlords are for wrongful eviction, security deposit disputes, and Fair Housing Violations.