Additionally, make sure that any lien-able service (in my area that would be trash and sewer) remains in the owner's name, otherwise a tenant can skip paying for that service, and you, the owner, will be struck with the bill when they leave.

Need to maximize deductions and depreciation over the remaining months of 2018 to significantly reduce taxes.

The positives are that I like $600 in cash flow, which has been mostly impossible for me to find in Massachusetts for the months that I have been analyzing properties and will probably remain that way for at least the near future. 

If the tenants don't want to sign a new lease, and remain month to month, I don't see why the property management company cannot provide them with a notice of rental increase. 

@Derek GibbsSorry, missed this earlier...yes, hut you have to work harder at finding them, while remaining conservative in your underwriting.

They don't really want to move, and we'd like to keep this house in the family.Can I buy their house for the exact remaining balance of the mortgage using a "subject to" sale AND they remain in the property?

The fist 24 months of remaining revenue would mostly go towards loan repayment before my potential partner and I take any distributions.

Short answer: The least possible you can to satisfy their requirements i.e. under promise and over deliver. 

Is it typical for the contract between a homeowner and the company to be one-year with the added clause that if I terminate the contract early because it doesn’t work out that I owe them their dues they would’ve received for the remaining time of the lease?

If the property will remain vacant for a time before the reno: Vacant Dwelling policy that includes Property & Liability2.