But before any of the above, there may be start-up costs and typical costs of doing business that may negate any potential benefits you may realize.

@Tyler Lingle cashflow depends on the Class of the property you buy.For the most part:Class A takes 3-5 year to positive cashflow, but you get highest relative rent & value appreciationClass B gives decent amount of cashflow & appreciationClass C historically is mostly cashflow, but at the lower end of relative rent & value appreciationClass D historically is all cashflow with zero or negative relative rent & value appreciation

Has anyone had any positive or negative experiences with Obsidian Financial?

BRRRR is a great concept.

I really don't see the negative of the DPA since, as far as I understand, the ones I'm looking at are forgivable after a certain amount of time (~3 years) and have 0% interest and no payments.

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

When analyzing properties, I'm finding that the monthly cash flow is often negative, which obviously sounds bad but doesn't account for my living for free in the other unit.

From the quick searches I have done, I feel it may be difficult to find someone local to me who specializes in FIRE concepts while using investments like real estate.

But like he mentioned, they'll likely say no or have a negative reaction. 

If I stopped receiving them, I would view it quite negatively.