-If the person dies later than expected, I face a financial loss. 

Food, water, shelter, the fundamental human needs.

the property with the most 3-5 year stuff should be on your short list to sell now if you're cash-strapped and you can at least cut your loss without having to inject more cash. 

Add the finance issues, level or effort it requires, loss of something from primary unit (even if it is just yard), and the amount of time between first capital outlay and initial income.In general, adding a ground up ADU in SF zoned area is a poor investment.  

In addition, the lender is going to incur costs including losses do to the time value of money if you stop paying and they have to take the property back.

I will only live in one of the units 4 out of the 12 months of the year because the other 8 months I will be with the Angels organization, during that period they provide a place for me to live and also food, so during those 8 months I would have more money I could save up and use in my house hack.

But how much damage will be done by hoping for the unknown and operating at a loss?

Their "Selena" which is foreclosed by Arbor is in east houston near ship channel and definitely in "theHood", their "Sophia" is in Greenspoint aka "Guns-point" and you can't get food delivered there without a police escort.

Often times the individual has long since recovered from what caused the derogatory in the first place--i.e. job loss, divorce etc.

Yes  buyers agents will make less , when you are hungry you will do what you need to to put food on the table .