All it takes is one non-payment or messy eviction to set you back months and even years in cash flow.

Any lender will see the income/loss in this manner even if the debt is not on your credit report.  

It is increasingly more difficult to pay of even one mortgage when you are cashflow negative, let alone multiple.

Even with a great opportunity, trust is the foundation of any partnership.In my partnership, we had already worked together on multiple deals—me as the agent and him as the investor buyer—so we had established a strong foundation of trust.

Also, focus on 2 years of job/income stability.Class D Properties:Cashflow vs Appreciation: Typically, all cashflow with little, maybe even negative, relative rent & value appreciationVacancy Est: 20%+ should be used to cover nonpayment, evictions & damages.Tenant Pool: majority will have FICO scores under 560 (almost 30% probability of default), little to no good tradelines, lots of collections & chargeoffs, recent evictions.

You might want to try tools like Stessa or Buildium for tracking, or even a simple spreadsheet to get started.

In some cases, after running the numbers, I’ve even faced potential negative returns, causing me to miss out on promising deals here in South Florida.That brings me to my question: I currently own two homes—one is my primary residence, and the other is a rental property.

This is not “student housing” in the traditional sense - even the vacancy risk doesn’t exist as it’s a 12 month lease / they work over the summer there, etc.  

Its a month to month and im in a weak position even to ask the tenant to renew lease now and they seem they are willing to stay they just need a solution to the issue.

While sophistication of your equity partners (private money lenders) will vary between residential and commercial, the principle of raising private capital is the same.You need to develop your own system which allows a constant stream of PML even when you don't need the funds and/or don't have an active deal under contract.For example; I raise private capital by offering free educational workshops for people with self-directed IRAs.