Using a 1031 to upgrade to a two-family could help you reduce or eliminate the $1,000 out-of-pocket expense you’re paying now.Also, condos often come with HOA fees that limit cash flow, so be mindful of their impact.

You can claim to be the best guy in the world at finding and analyzing deals, but when the market turns against you, and you just went all-in, even on the best relative opportunities that market had available at the time, there is nothing you can do to prevent losses, especially if your debt has a maturity date that will force your hand.Timing the market is an interesting concept. 

Making the wrong hire, overlooking the risks, taking on too much debt.

Clearly the note is more than just evidence of a debt, right?

Buying in your backyard eliminates so much for you.What strategy do want to follow?   

We have no debt and good credit scores, do we have any options for making this work?

We buy at a discount and pledge our legal right to collect the debt (a collateral assignment agreement) as the collateral for the private capital loan we take out, which is backed by the value of the real estate securing the 1st loan.  

Though it may cash flow well based on their current debt service, when you compare the income it produces to the equity they have is it actually even a good investment for them from an ROI perspective or would they be better off liquidating and redeploying?

Unsecured personal debt is often from institutional sources, but at rates of 9-20%, fully amortized over 3, 5, or 7 year terms (not interest only).

If you can purchase this home with private money or seller financing and get a $110k loan, then you could do a rate/term refi right after so do a 90 or 120 day note to secure the property and get it in your name, then refi into long term debt using the full appraised value.