This property is gonna cash flow over $1000 a month after we're all said and done with utilities mortgage and more.

TikTok probably the 3rd largest in monthly viewership, those eyeballs need to go somewhere.

. :) A zoning change can take up to 6 months, approval isn't guaranteed (despite Aldermanic support), and potentially cost a lot of money (architectural site / floor plans & dimensioned elevations, zoning attorney, holding costs, etc.) 

It'll likely take a month or two assuming that the loan is with one of the large servicing companies that move at a glacial pace. 

I’ve recently talked to a property manager and a realtor for my San Diego property and found that going with a manager would put me in the hole 1k a month MINIMUM.

I've included an example below to help illustrate this.So different lenders have different rates (which do vary even for DSCR loans) but these are factors they all consider.See example below:DSCR < 1Principal + Interest = $1,700Taxes = $350, Insurance = $100, Association Dues = $50Total PITIA = $2200Rent = $2000DSCR = Rent/PITIA = 2000/2200 = 0.91Since the DSCR is 0.91, we know the expenses are greater than the income of the property.DSCR >1Principal + Interest = $1,500Taxes = $250, Insurance = $100, Association Dues = $25Total PITIA = $1875 Rent = $2300DSCR = Rent/PITIA = 2300/1875 = 1.23If a purchase, you also generally need reserves / savings to show you have 3-6 month payments of PITIA (principal / interest (mortgage payment), property taxes and insurance and HOA (if applicable).

BTW there is a free trial and the Starter monthly plan is $119.It also allows you to search through consumer information such as property owner "credit worthiness," Credit card usage, buying power, age, language, family members in the house, and many other fields that are above and beyond property characteristics, which is unique.

But…There’s ZERO chance I would rent by the room for $600/months more.

Fix it before the next month.

Same as if you are inactive for a month between brokers, something like that.