That said if it gives me more freedom to make the right career choices or it allows me to act on investment opportunities in the next couple years, maybe it will have been worthing eating additional expenses for the first several months.  

Hopefully they at least buy a few as vacancy would mean you don’t eat that month! 

This is a tough poo poo, you gotta eat the cost and make sure you hire someone that isn't a hack.

You can try and cut the middle man out on a sub2 pre-foreclosure, but it's as tricky as trying to eat an ice cream cone in the pits of hell.

Leverage increases ROI, equity eats your cash flow assuming you place any value at all on your money.

They were actually eating out of the fridge below the morning the sheriff evicted them.

- the mortgage alone might eat that Rent....and then there are taxes, insurance, maintenance (OOS - paying contractors). 

And I’ll have to eat the expense of a double tear off on a big roof.

I wish this wasn't the reality of the business I chose but it is dog eat dog out there. 

It's easy to make a profit til the one mistake eats all of it, and that is just foolish when  mentor might mitigate that expense.