I've used Airbnb and they have reimbursed me for repairs when a guest does damages, but they take a lot of time and the reimbursement is not always what I expected.

Was the owner doing his own repairs and hiding the costs?  

Sometimes David makes mistakes with repairs but I've never known them to try and cheat me.

And generally, they took longer to rent, longer to sell, cost relatively similar (maybe moderately less) to repair and rehab as other less affordable areas, and had more turnover than desired.I also have a good friend/investor who owned over 100 sfr doors in the Detroit area that they were acquiring amazingly cheap, then rehabbing them.

(After Repair Value; is this another person you have to hire?)

how are you getting an accurate representation to the costs to repair the property?

Focusing on generational wealth is probably not your best prospect.A better focus might be running the property in a professional manner, maintaining the asset value of the property through appropriate repairs and upgrades , learning some best practices for management , and having enough cash reserves to keep the property from being seized by the bank in lean times .

That has less to do with crime (in the area that I live I don't see it as a big issue) and more to do with taxes and tenant-friendly laws.For any area that is higher crime, you should budget for higher vacancy (and significantly higher vacancy if you don't set tight screening standards and have to evict a tenant) and higher repairs and maintenance.Good luck!

There is a retaining wall that is bowing, which I had an estimate done during the purchase contract which the seller dropped the sales price for that repair.  

Converting your single-family home into a rental property involves several considerations to protect yourself and ensure smooth operations: Establish an LLC:Liability Protection: Holding the rental property in an LLC can protect your personal assets from potential lawsuits related to the property.Tax Benefits: An LLC can offer tax advantages, such as pass-through taxation, where rental income is taxed at your individual income tax rate.Insurance:Landlord Insurance: Ensures coverage for property damage, liability claims, and loss of rental income.Umbrella Policy: Provides additional liability coverage beyond your landlord insurance, offering extra protection.Deductions:Mortgage Interest and Property Taxes: Continue to deduct these expenses.Depreciation: Depreciate the cost of the property over 27.5 years, excluding the land value.Maintenance and Repairs: Deduct costs related to maintaining the property.Property Management Fees: Deduct fees paid to the property manager.Filing Taxes:Schedule E: Report rental income and expenses on Schedule E of your tax return.Separate Accounts: Maintain separate bank accounts for rental income and expenses to simplify bookkeeping.Lease Agreement:Solid Lease Terms: Ensure your lease agreement is thorough, covering rent amount, due date, late fees, maintenance responsibilities, and eviction terms.Legal Review: Have the lease agreement reviewed by a real estate attorney to ensure compliance with local laws.Tenant Screening:Background Checks: Perform credit, criminal, and eviction history checks on prospective tenants.References: Contact previous landlords and employers for references.Property Management:Regular Inspections: Schedule regular property inspections to ensure it's being maintained properly.Maintenance Fund: Set aside a reserve fund for unexpected repairs and maintenance.Moving Out of State:Communication: Maintain open communication with your property manager.