@Jennifer Taylor First  answer this: Do you currently operate your properties with all proper permits and licenses?

We operate a small retail business out of commercial space in the building with the 4 residential units, which pays me a W2 salary and my wife has a part time W2 job at a vet clinic. 

Connect with @Jillyan MacMorris she's an experienced MTR operator in Chicago

.- Tech-Driven Operations – Using property management software for things like rent collection, maintenance requests, and communication has made everything smoother and saved a ton of time.- Curb Appeal & Upkeep – First impressions matter!

Rise48 seems to be a good operator. 

The bigger and more diverse your business, the more cumbersome managing multiple policies can become.Administrative Burden: If managing multiple policies is consuming too much time or resources, consolidating may be a way to streamline operations and reduce the workload on your team.Negotiating Leverage: When your business reaches a certain size, you may have enough premium volume to negotiate better terms by consolidating with a single carrier.Final ThoughtsConsolidating your insurance portfolio into a scheduled program can offer significant advantages in terms of cost, simplicity, and risk management.

Cost segregation can help boost cash flow, create substantial tax savings, and increase the profitability of the warehouse operation by accelerating depreciation.A cost segregation study is a strategic tax planning tool that separates the assets that have a shorter useful life and can be depreciated over 5, 7 and 15 years from the residential rental property or nonresidential real property that are depreciated over 27.5 and 39 years, respectively.

Like everything else, there are tradeoffs.However, you mentioned being in an area with students, so SFH's in your area may operate more like multifamily units anyways with higher turnover.

Asking for and evaluating T12 is much more relevant to larger MFR with management than M&P operations. 

These are small enough that they are still operated by ma-and-pa operators but they are typically easier to find funding, operators, and contractors for.