We also wanted to fill in any gaps in our understanding of the BRRRR strategy before jumping in head long. 1) Their coaching product was detailed and easy to understand.

Bottom line is you have to have a solid grip on what properties rent for in your market - not only direct comps to what you have but also what's above and below you, because tenants can and will move based on affordability both ways ("downsizing" to save money or "upsizing" because an extra $50/100 gets them a much nicer place).Once you intimately know what your market is, and what's available, you can compare what you are charging to those figures and adjust accordingly.

Without a PM you can afford to pay top dollar for service professionals as needed.  

They paid the deposit and prorated rent, but they couldn't afford a full month of rent a week later.

I will purchase this 4-plex through an FHA Loan with 3.5% Down Payment and live there for at least 1 year until I can afford my next multi-family!

I’m stating to look around some of the smaller markets outside of Boston, starting to dive deeper into market research to see if some of the more affordable areas are sustainable for rentals.  

>Sacramento remains affordable at $1,850/month, with minimal growth.

As long as you can afford to make the repairs within the next year or so and you're not spending more than the house is worth, I would move forward with the purchase.

He's the CEO of a company that builds healthcare facilities, and you rented him a "fully furnished luxury executive rental," but then you said he's broke and couldn't afford to give his kids Christmas presents?

Hard Money Loans.There are other niche products but those are also in general order of cheapest down payments and interest rates typically.Good luck!