I am in a co-op program which means I rotate between classes and in-field work each semester.

And you do have the sticky situation of explaining why you went month-to-month from the get-go.I recommend you research the renters' assistance programs in your area and help them get on these plans, while keeping them a long term tenant.

Corporations know how government will react when more people are homeless, which is by expanding housing programs.

@Ben Gradert Aloha Capital has some interesting programs too

Some that are more aggressive at deploying their capital can start with 75 to 80%.FHA is such a picky program it's really easier just to accumulate more cash and bypass all their rules and hit up conventional primary residence for 95% LTV.

That way if she doesn't move you can get the Execution rather then starting the court process at that time.One more thought, since this is Chelsea, there are various programs in place that will help tenants with various costs, including moving costs (and first, last security at a new place) You may get a call from Legal Aid as well that they are helping her. 

My younger self would be driving Amazon by day at $25/hour and taking online accelerated courses for business administration BA and MBA, and get certifications in project management like SAFe Advanced Scrum Master or Certified Scrum Product Owner. 

The Certificate of Insurance must be updated regularly.

Any recommendations on a plug-in program for our multi family investors?

Prior to closing you need to have an estoppel certificate stating rents and verifying terms of the lease, security deposits and any oral agreements.