You can really pick where you want to be on the "comfortability to profitability" scale here where I felt like those options in most markets were limited. 3) it's a great place to live all-around.

You don’t have a large enough portfolio of houses for a lender to feel comfortable without a personal guarantee. 

This will impact your costs and time commitment.Risk Tolerance: How much risk are you comfortable with?

Get out of your comfort zone.

The downer is that financing through an LLC would mean “commercial loan” which has a high interest rate of nearly 9% in today’s high rate environment.

Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

So it's really what you are comfortable with and what your investment thesis is. 

I acknowledged his concerns but was unable to resolve the issue.Since the tenant moved in, I have experienced escalating issues with his behavior, including:Lease Violations:Moving items without permission (furniture, safe, carpet cleaner, TV from his room to another tenant's room).Accumulating boxes in the garage, potentially exceeding the agreed-upon storage space.Installing a security camera in the common living area, which is a direct violation of the lease agreement.Failure to submit a work order for alleged issues with the smart lock, as required by the lease agreement.Behavioral Issues:Aggressive and confrontational communication.Unfounded accusations and personal attacks.Refusal to communicate through agreed-upon channels.Loud and disruptive late-night behavior (banging on the door, kicking the door) due to alleged difficulties with the smart lock, often accompanied by profanity.Harassment of my son, the designated on-site property manager, by making disparaging remarks about me and refusing to cooperate with him.Potential for Neighborhood Disruption: The tenant's late-night outbursts have the potential to disturb neighbors, although no formal complaints have been received.Unreasonable Demands: The tenant unreasonably demands advance notice of my access to the property for storage purposes, despite the prior agreement and my right to access common areas and my own storage spaces.Safety Concerns:While the tenant has not directly threatened us, his actions, including the harassment of my son, have created a concerning and unsafe environment for my son and me.Goal:My ultimate goal at this point is to evict the tenant due to his ongoing lease violations, concerning behavior, the harassment of my son, and the potential for neighborhood disruption.Questions:1. 

Get out of your comfort zone.

This is all indicative of a low interest rate environment.