Any home you buy with $20,000 is likely going to be a fixer-upper, which means it can be heavy on repairs, turnover costs, vacancies, etc.

Cash-flow is for "keeping the lights on" as in covering operational expenses to defend against any need for additional capital investment. 

If your property manager is not listed as an additional insured, they may not be covered under your policy in the event of an incident on your property, leaving both of you potentially exposed to liability.It can save you money.If your property manager is not added to your insurance policy as an additional insured, they may be forced to purchase their insurance policy to protect themselves.

I would look at it in terms of whether you can afford a worst case scenario where you're covering the deductible and have a credit line or cash to front the re-build cost and getting reimbursed from insurance afterwards.

By adopting the house-hacking method—living in one unit while renting out the others—we plan for the tenants to cover the mortgage and gain valuable property management experience.

Yes you have insurance, but it may not cover everything.

Related damages:When tenant took possession, the living room had a vertical blind set apx 70” long (covering two windows.)

I plan on being on the road here for work in the next day or two and wanted to try and make sure I have everything covered before I leave.

If it's way out of whack with the market average, dig deeper.Debt Service Coverage Ratio: Key for nderstanding if the property's cash flow will cover financing comfortably.Historical Vacancy Trends: Especially in areas like Chicago, where local job markets fluctuate, knowing vacancy trends can help you anticipate rough patches.Rent Growth vs.

Umbrella Policies are good, but they are not an asset protection tool, they only cover litigation/damages after you’re already in litigation or found personally liable.