Detroit can be tricky to analyze, and some deals that look good on paper might have hidden pitfalls (taxes, rehab surprises, etc.).

Drivable to the Bay Area, much lower property taxes (that DON'T reassess on the sale), much friendlier tenant/landlord laws, strong population and job growth, strong appreciation, and also anchored by the tourism and wealth of Lake Tahoe. 

If you need financial help, ask under the "Finance, Tax, and Legal" forum.

Additionally the suburbs have higher taxes compared to Chicago proper.  

They are going to look at tax returns, they aren't so much looking at it month to month basis.

Is it to build up assets, is it to make additional income, is it to reduce your monthly housing spend and save more money, is it tax breaks/benefits? 

Take a look at the rents for both sides vs current mortgage payment (if any), new payment on the cash out or HELOC, taxes, insurance and HOA (if applicable).

If we are checking property tax records, should we not buy a home where different LLCs (investors) have owned it and sold it every 2 to 3 years?

Hey Becky,When you sell the property, the LLC will still technically own the property until it is formally restructured, so you will need to amend the LLC’s operating agreement and update its ownership structure to reflect the change, ensuring the absent partner’s interests are properly dissolved, and taxes are handled accordingly.

It’s looking like this will cash flow neg just with est mortgage payments plus insurance and taxes of $1100ish (after renovation), property management of $120.