My personal assessment of the overall economic risks has hit a tipping point.  

The original owner has a ton of exemptions so she only pays $400/ year on property taxes.

We have a Mac and wanted to use Quicken for personal/rental finances.

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.

If you are raising money you will need to register the exemption with the SEC, and it will depend on whether you are using accredited or non accredited investors. 

Personally had great experience with Charleston's housing authority.

If it does require something in person, maybe your cleaner can be paid to do it?

as  PML personally your first positions are simply too high to take the risk of being in Second position.

The more I learn, the more I understand why a person would want to sell and buy this way:1.)

If you buy the property and live in one side for two years you would get the full primary residence exemption on that side.