On a positive note we did build a new house to the specifications of a specific tenant. 

For path #2, you mean purchase & renovate a 3-5 unit building right?

@Kiryl Ulanovich,You're on the right track:Get Pre-Approval from Hard Money Lender – Know your terms and limits upfront.Find a Deal Through a Wholesaler – Verify numbers and ensure it meets your criteria.Review the Assignment of Contract – Confirm terms, earnest money, and contingencies.Conduct Due Diligence – This includes an inspection (if allowed), verifying ARV, and rehab estimates.Submit to Hard Money Lender for Final Approval – Lender will review title, contract, and property condition.Title Search & Clear Any Issues – Ensure a clean title before closing.Close Through Title Company – Finalize funding and take ownership.Consider also lining up contractors early for a smooth transition into renovations.

Conducting inspections and due diligence on the condition of a property to derive realistic estimates for repairs is still the key.

The buyers did a long inspection, multiple days... made a huge request for concessions based on what we knew to be purely made-up issues.

The ways around that are to build a business around supporting their voucher and inspection program and spending no small amount of effort ensuring they are smoothly servicing your rentals. 

Connecting with them directly will help you get a better sense of voucher amounts, inspection standards, and timelines.

Do you rely on inspections, local contractors, the agent, or property managers to get eyes on it?

It’s ok you can go and inspect.

The inspection showed more issues than we expected but the seller wasn't willing to negotiate so we cancelled in the due diligence period.