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.

I am currently going throught the lending process and research some of my top locations.  

Especially if you're like us and have STR in locations with no cell service!

Depending on where we will pursue a location.

These are not nationally known locations, but still pretty popular drive-to vacation spots for Minneapolis, Chicago, Milwaukee and Detroit metros. 

Quote from @Michael Carter: Looks to me like Barryvilles location is really only suited for STR.

I’d appreciate some guidance on a few matters regarding my investment properties.I recently purchased several properties in the following locations:•Ft.

You are purchasing assuming market rents (set by the condition, amenities, location, etc. of the property) so agree that a seller would likely question a request for a lower price or their receiving less at closing. 

To succeed in Cleveland's short-term rental market, research local regulations, analyze potential locations, find ideal properties, build a network, plan renovations, stay connected with BiggerPockets, focus on modern bathrooms, cozy outdoor spaces, and practical amenities.Good luck!

The no state income tax doesn't really apply when you are comparing to other investment locations.