@Ryan KonenOne that we believe goes overlooked is courage and the courage to speak up if you have an opinion as well as be open to feedback.As a ceo I am not perfect and do not know it all, If someone disagrees with me - then say it - and know there is not a backlash or repercussions for disagreement.

I would take a look at a couple different things, at least speaking from a tax perspective. 

But at the end of the day, well located properties in which the owner has ample liquidity to ride out long-term cash flow negative periods, rarely lose money.  

.$10k STR rent on $1.3m property at 80% LTV  will be negative cash flow when properly allocating for all the expenses.  

Quote from @Nathan Gesner:Even on a property with negative income for a year and has been on the market for more than 90days?

I got a 2013 Toyota Corolla for $17k, so unfortunately, even if I trade it in I still have about $6-9k in negative equity on the car that I’ll still owe.

rental 1 - 2k overall after depreciation, expensesrental 2 - 10krental 3 - NEGATIVE 15k Overal rental loss/profit for year (after depreciation, expense, etc) for the 3 rentals is NEGATIVE 3k that cant be written off, but carried over since +150kOr is it ex. 2Rental 1 - 2k and Rental 2 - 10k are added for 12k.

Thats with my cheap subs and me paying them cash using a GC this would be a $70k rehab and negative equity. 

The bottom line assumes that your overall cash flow will go up from acquiring this new asset, which existing property, when you leverage will have the smallest negative impact on your overall cash flow. 

Your estimated first-year NOI is $29,040, but after loan payments, you're left with a negative cash flow of -$9,126 and a DSCR of 0.761, indicating the income doesn’t cover debt service.