Quote from @Richard Bautista: Good evening,Just saw Cleveland, Ohio has relatively inexpensive houses which has the potential to cashflow.

Do you think it's common for a tenant to sue for an amount greater than insurance can cover, then take your property or even your personal assets? 

We simply include the tax on the invoice sent to guests, which makes it easier to track and ensures we're covered for tax purposes at the end of the year.For Chicago, I’d recommend checking directly with the city’s tax office or a CPA, but generally, you’ll need to register with the city, collect the hotel tax from guests, and remit it on a regular schedule (likely monthly or quarterly).

:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, 1-3 years for positive cashflow, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, immediate cashflow and at the lower end of relative rent & value appreciation.

The city also benefits from a relatively low cost of living compared to other major cities, attracting both renters and investors.

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I've tried to include relative information, without writing a novel. 

Keep in mind that I am selling them as affordable fixer uppers and usually only address any health, safety, and functionality issues.

Make sure your lease clears you of liability, in case they are not covered.

Most occupied property insurance policies will cover "vandalism and malicious mischief" but there are different forms of policies so you'll have to ask.