Think roofs, old pipes, heat repairs, termite damage etc.

Make sure you don't mishandle your deposits or you may find yourself owing the tenant 3x the deposit (read up on treble damages in the context of MA Security Deposits) 

Lastly, after you receive advice from other Chicago area SLH operators & the local municipal agencies that will not only save you time but direct you towards ways to save you money, you are going to likely want to register your business as an LLC with the state and obtain the proper small business renters Insurance policy under your LLC’s name (if its just a 2-3br operation the policy monthly premium  cost will be very low and will shield you as an individual from the very probable situation of being personally liable for the behaviors, damages, & actions of a traditionally high-risk short-term tenant group bc no landlord’s homeowners insurance policy will cover any damages or personal liabilities that will occur when they discover the nature of the operation.

Its definitely a bit complex when it comes to varying neighborhoods and blocks but if you're ever interested don't hesitate to shoot me a message.

It's important to look at the long term outcome, being an unethical wholesaler can damage your future reputation among the RE investing community.

Originally posted by @Jocelyn Doumani:Did you have the Tenant provide you with a Renters Insurance policy, just in case the Tenant does damage the property?

It might be a good idea to have your lease forbid blocking windows with foil, or other opaque items other than curtains or commercially available window blinds (that are not flags or political).Drug dealers, and fake drug dealers tend to block windows so no light can get in, and no Police Officers can see in.As far as flags it's not a proper venue for National flags, and gives you leverage in case someone decides to hang flags offensive to some (such as public display of WWII Axis flags, or socio/political flags) that might be detrimental to your rental business.Good Luck!

For a security deposit with an inherited tenant, I will only subtract for NEW damage that happened after I bought it. 

Buy rental properties with roof damage south facing.

I recently won monetary damages from an eviction hearing for a little over $7,000.