The Seller guarantees that the property will be clean and unoccupied within 14 days of the valid offer.

Cash flow would likely be a little higher and more marketable for a multi if prospective tenants feel like they have somewhere that’s their own, instead of just living in a room in someone else’s home.

My concern is I tend to be less risk adverse especially with short term losses if the long term gain is worthwhile (i.e maybe the property might not cash flow today but it gains more equity).

I have a house very close to the Cleveland Clinic that I am thinking of doing this for extra cash flow.

It's a math problem more than a qualification problem, but you may want to cap your loan amount to get a better rate (and cash flow) vs maxing out and having a little more cash, but really bad cash flow.

In the basement I hung streams of toilet paper....and when the room is still, no heat flowing - I notice the toilet paper swaying a little bit.

I also rented my primary residence in Denver and have $800/mo cash flow on it.  

Does it cash-flow when you factor in expenses to hold as a LTR, MTR, or STR?  

Cleaning, restocking, rebuying broken furniture, hanging up new art, meeting with a general contractor, etc. your kids will be expecting the beach, and yet you will be hanging up wall art. 

Real estate generates a return through cash flow + appreciation.It appears that cash flow is negativeAppreciation appears to be 0% over 2-3 years based on zillowThe question is what you beleive the future will hold for cash-flow and appreciation.Cash-flow will likely continue to be negativeThe question is what do you think about the appreciation for the bay area.If the property continues to stay at $850,000, it will likely not be a good decision to hold on to the property.If you think the property can appreciate to $900,000, $950,000 over a few years, then it can potentially be a good reason to hold.