I perhaps naively went ahead with the registration and inspection after completing purchase of the home, and wound up with a hefty repairs bill of around 3k.

Analyze potential deals by estimating the After Repair Value (ARV), repair costs, and total expenses. 

Risk Mitigation: What strategies do you use to mitigate risks when investing in older properties in Cleveland, especially in terms of unexpected repairs or property management?

I feel like marking up repairs is paying twice.

Each of the 5 warehouses on this campus will require updates (construction of offices/bathrooms, roof repairs, paint, siding repairs, new penetrations for doors, updates to electrical, insulation, and extension of water and sewer). 

There are never full photos of the mechanicals and basement and roof line so you will never have even a bare inkling of what the potential repairs will be.

It couldn't hurt to call a couple attorneys right away to see what they say in terms of cost and suggestions for dealing with this quickly.In terms of mitigating any legal issues with your tenant be sure you are documenting every conversation you have had with the HOA in terms of asking them to make the necessary repairs.

Even if you break even, you will lose money every month it sits vacant, when you need repairs, property management, etc.

Repairs were needed and were finished by early december.

Repair costs in first 1 month of owning (this is renovated house done by seller, not me.