I'm not 100% committed either way between the income benefits of multifamily vs. the reduced headaches of SFH tenants.

Even though classes would all be remote, All of us were for sending him off to school and were thrilled when he won a lottery for the reduced capacity dorm.  

That makes zero sense unless you are trying to reduce risk and you have a very consistent NICHE market for those under $100K Sec 8 units.  

Lots of new supply now with reduced demand.

With that in mind, which approach do you think works best:1.Use property management software (PMS) as an intermediary to automate payments and fee splits while reducing legal risk and simplifying operations?

Fortunately - we have a good relationship with our servicers and can get frictional matters that arise rectified/resolved relatively quickly, but the frequency of said matters could certainly be reduced.

Per the mutual agreement between the Lessor and the Tenant, the Lessor has agreed to reduce the monthly rent from $3,200 to $3,100, allowing the Tenant to repaint portions of the house at their own expense.

Raise rents, reduce expenses (shop insurance, appeal taxes, refinance, etc). 3.

This has significantly reduced the cash flow across both portfolios.

Personally I’d stick with SFR or at 4 units or less for preferred financing and to reduce risk of the exchange failing.