I was also planning to work for a property managing firm to learn the ropes of the state and local codes while continuing to invest.

With the way my portfolio and pipeline is arranged I can understand why the construction management or brokerage verticals are most enticing but it still feels too transactional which is what I want to avoid.

If the repairs are manageable and you’re getting at least a 10-15% discount, it can be a great deal—but avoid properties with major structural failure or uncooperative sellers.

I manage and own some STRs. 

I actually have two south side chicago properties right in that pocket of Greater Grand Crossing.The key here, more than anywhere else, is proper tenant screening and property management. 

The state will get its pound of flesh and my liabilities were better managed by executing perfect permitted work and excellent insurance.I'd sincerely recommend having a savvy CPA, Lawyer & Insurance broker.

I don't even need a management company.

Either myself or project manager wen I don't have time, because most contractors need daily supervision.

The key is to standardize property quality and management systems, which would appeal to buyers seeking scale.If you’re thinking long-term, holding these properties for cash flow while leveraging local appreciation is also a strong play.

I would run this by your realtor/property manager to get clarification.