@Lisa James If your plan is to find a single buyer to step into your shoes, there is no contingency necessary (for this particuar issue) -- single purchase agreement, freely assignable, covering both parcels.

I wanted feedback prior to doing so and was curious as to what others, such as yourself, would do if you were put in my shoes. 

@Kar Sun,No-- if I were in your shoes, I would not rent to them. 

Thats a fantastic book for someone in your shoes.

I was afraid that she was going to file bankruptcy when she got over loaded and the BK court would force me to let her live in my rental without rent until they settled her issues.Her debt was mostly credit cards, used the $ on trips, eating out, expensive clothes and purses and shoes. 

If I were in your shoes, I would continue to save and work on your credit.

If I were in your shoes I would send the letter to your attorney and let them handle it from here.  

So if you were in my shoes what would you do?

This is going to depend on your risk tolerance and preferences, but I'm happy to provide my input..If I were in your shoes, I'd do the HELOC because of your interest in BRRRR. if you were trying to do a long term rental, I would do a cash-out refi on your primary residence. 8 years is a long time to wait to do 1 deal, so I would personally shy away from depending solely on cash flow.

If I were in your shoes, I would look for a house near transit access that has the potential for a legal rental suite.