The way I see this is :1. not utilizing the calculator well enough (eg. undervaluing my rent estimation) 2. there is no good properties in the area to invest. 3. other issues that I may not see (blind spot). 

My issue is my credit took a hit during renovations and I had to evict someone that wasn't supposed to move in a property.

While insurance has covered some costs, the process has been stressful, even with a property manager (their responsiveness to these issues has been slow).

But with zero enforcement since they don't issue or require STR permits.  

No issues with zoning?

In Mass you can avoid sprinklers by using 2015 IEBC chapter 14, a quick fire safety analysis of the building and exits. 

when there is an issue someone will make a big deal over it.

None of the expenses are exact but I am hoping to verify that my big picture idea (line 35) is correct and that I'm not missing any glaring issues.

That wouldn't be enough to just decide to move out for FNMA, but with a legitimate employment issue you've clearly demonstrated an intent that met the loan covenants. 

Let's explore some effective approaches for managing investment properties:With a Property Manager:Screening and Selecting Tenants: Entrust your property manager to handle tenant screening, background checks, and selection, ensuring reliable renters for your investment.Rent Collection: Property managers can ensure timely rent collection and handle any late payments or lease violations professionally.Maintenance and Repairs: Delegate routine maintenance tasks and repairs to your property manager, who can coordinate with contractors and vendors to keep your property in top condition.Tenant Relations: Property managers serve as the primary point of contact for tenants, addressing their concerns and ensuring a positive rental experience.Lease Enforcement and Evictions: Trust your property manager to enforce lease terms and handle the eviction process if necessary, following legal procedures.Financial Management: Property managers can handle financial tasks such as budgeting, accounting, and financial reporting, providing you with regular updates on property performance.Without a Property Manager:Self-Management: Take on the responsibility of managing the property yourself, handling tasks such as advertising vacancies, screening tenants, and collecting rent.Outsourcing Specific Tasks: While not hiring a full-time property manager, consider outsourcing tasks like maintenance and repairs to trusted contractors or service providers.Utilizing Technology: Leverage property management software and online platforms to streamline processes such as rent collection, lease management, and maintenance requests.Establishing Clear Policies: Set clear policies and procedures for tenants regarding rent payments, maintenance requests, and lease terms to minimize conflicts and misunderstandings.Regular Inspections: Conduct regular inspections of the property to identify maintenance issues or lease violations early on and address them promptly.Building Relationships: Maintain open communication and positive relationships with tenants to foster a sense of community and encourage better care of the property.Whether you choose to hire a property manager or manage the property yourself, effective communication, attention to detail, and a proactive approach to property management are key to maximizing returns and maintaining the value of your investment.