I've stayed in properties that offer a small selection of drinks or cheeses from local farms but have never seen it scaled to other aspects of the property.I'm wondering if any STR investors out there employ a similar arrangement?

Even if newer buildings can't price rents as low as yours, they might offer amenities or modern designs that attract potential tenants.Local Economic Factors: Consider local employment rates, major employers relocating, or any changes in the local economy that might impact rental demand.2.

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.

I would employ a property management company that can handle this for you, like the one I work for as an agent.

The company's legal counsel has said a guarantor is not needed, citing the company's annual revenue and an employee, effectively, being unwilling to cut a check on behalf of their employer.

You might also be able to employ a short term rental strategy to increase cashflow-- sporting events, conferences, homecomings, graduation, etc. always attract people to the area.Ask around and try to find people who are investing in Amherst/Northampton and connect with agents in the area to see what's working.

However, if the applicant only has a low credit score but more than sufficient income, rental history, steady employment, etc., you may consider conditionally approving with a higher security deposit (or alternatively, use an insurance policy - "fee in lieu of deposit"), first and last month's rent.

I have been looking to employ the strategy for my next buy.

Conservatively, I think we'll be making around $80-$100k/yr ($50-$80 W2, $30-$50 self employed). 

I would call a Broker you trust and ask them for a referral to a few Title Companies that employ attorneys (not all do, at least not in Maryland).