Right now, the best offers around me are for some 1.3-4 million, that only generated around 100k per year gross, so there would be a high chance of not cash flowing, and paying money, especially with a commercial loan (these buildings have more than 4 units).I was thinking that although the rental itself does not generate money, I would be able to deduct the mortgage interest, and depreciation from my personal w2 income and would be net positive.

Your looking at this really cool and unique position your in, and focusing on it as a problem. 

I’m not looking for a step-by-step guide, but I know I’m not the only one in this position.

We pride ourselves in keeping the forums positive, helpful, and focused on real estate (please, no politics, religion, etc.).

This creates two loan payments ($100,000 of equity and $300,000 on the new mortgage).Key NumbersHome Equity Loan Interest Rate: 6%Mortgage Interest Rate: 7%Rental Income: $3,000 per monthExpenses (management, taxes, insurance, maintenance): $800 per monthIncome and ExpensesMonthly Rental Income: $3,000Monthly Expenses: $800Monthly Mortgage Payment: $2,000ExplanationThe investor earns $3,000 in rent each month.They pay $2,000 on the investment property mortgage and $800 on other expenses.This leaves $200 profit each month or $2,400 per year.However, you have to pay $6,000 interest on the equity borrowed.This leaves you with an annual loss of $3,600.While the rental property generates positive monthly income, the interest cost of borrowing the initial $100,000 results in an overall loss.

I don't know if they still do it but if memory serves a few years ago TD Bank would do a HELOC on a rental in second position but only if it was titled in someone's personal name. 

Depending on how far values decline is the difference between a partial loss and total loss. in essence its the same position of those who make second loans behind the first or third position when pref goes in front of you..

Unfortunately, given current and foreseeable prices and interest rates, I will not be in the position to buy anything else anywhere I’d want to go. 

Has anyone been in a similar position, or has had success offering this type of agreement to a previous owner of a property who has not yet voluntarily vacated?

People in the group are great, positive, and supporting.