Let's assume you are only looking at deals that you could buy cash.The biggest factor that goes into the decision is whether you are taking on positive or negative leverage.  

However, I'll never second guess what my well-connected and trustworthy contacts on the ground tell me, especially if it's very (negative).

what i'm finding is that, if i BRRRR successfully and then refinance into a DSCR loan, almost every property is break even or slightly negative. 

I am not trying to be negative or a Karen, but being real so you can analyze all your options on what course of action you should take for your business and what risk level you are comfortable with.

It is a tough buy and hole RE market everywhere but markets like San Francisco are particularly challenging in the short term due to the poor cash flow (negative cash flow).  

Avoid negativity, man. 

Your app concept sounds promising!

However, when you factor in the HELOC, we have a negative / break-even cash flow (HELOC payments are about 25% of the revenue from both).

Keep in mind that many of these cheap homes are selling for less than a third of their insurance replacement value, which really means that the land has negative value - let that sink in.Most buyers who can actually qualify for a mortgage will get a PA for $200-300k and desperately want to upgrade their life.

Just remember: most negative reviews are written by problematic tenants.