@Stuart Udis you say things like a “red flag” almost as if you don’t believe what I am saying or think that I am making things up.They are 2 different properties.

IF the City does not limit to four total, there is a scenario where the City MAY allow up to 10 total units on single family zoned parcel

I would be very careful about what neighborhoods you invest in, though; Cleveland has some serious war zones. 

On paper we were slightly in the red but much of that is due to one-year expenses/repairs & allowable transportation costs to get up to the property for work days ourselves. 

Be an area expert on contracts, zoning, value add components, contractors, and so much more. 

Get out of your comfort zone.

If you are not familiar with Scott, Scott was the Executive Director of the Opportunity and Revitalization Council, which was tasked in part to support and advance Opportunity Zone tax credits during the first Trump Administration.

Red tape with trying to get the HOA board to approve repairs.

Get out of your comfort zone.

Yes, one approach is to continue with finding other cash flowing property.Let me suggest some other ideas for you to ponder, especially since you've also mentioned you are looking hard at DST's:What about Opportunity Zone funds?