Now today, I learned through the neighbor she currently lives next to that she hasn't kept up the house, has been problematic, and apparently had eviction notices filed by her current landlord.

So you need to remember that there are about 4- 6 big box lenders that fund most of the Hard Money loans and then you have thousands of brokers selling their products and lots of times someone thinks they are dealing with a lender but they are not, they are dealing with a broker who has a lending sounding name and this broker is set up with an account at a few different lenders. 

Can't answer without knowing how noisy it is vs: location, price, rents, condition of side by side or town house

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.

So I basically would want a person who looks at the whole house and gives me the appraisal cost, the areas that need fixing (ex. kitchen cabinets, tiles, bathrooms, plumbing, electricity, etc.), and how much the cost would be.Then this way, I could decide to proceed or not based on the assessment.

Sokun So, it's not uncommon for property managers to prefer setting up OTA (Online Travel Agency) listings on their accounts to streamline their management systems.

We live in the main house which along with the garage was built in 1927.

A fully paid off property which now should be worth at least $300K with appreciation, I can access 75% of that with a cash out refi so roughly $225K - refi costs.To me, its a no brainer to do bi-weekly IF you plan to keep the house for that long AND you do not plan to refinance (rate or cash out).

The challenge for present day investors is with elevated mortgage rates and record high housing prices, the carrying costs and incentive to invest now can be restrictive. 

Have you thought about renting out rooms in a house instead of STR or renting the entire house?