If you ever make your way down towards Rock or Dane County, I would love to meet for lunch or coffee.

Coffee shops like the "to work" side.  

If you make $15-$20/hr working an extra 2 hours per day that could be an extra $200/wk or $800/mo. $800/mo can get you a $100k mortgage. 

1 thing I would say is even in Baltimore inventory can be an issue. 

What would be an appropriate way to begin negotiation?

DSCR would be an option, however, if you can qualify for a full a documentation loan your rate and terms (like your upfront closing costs and pre-payment fee that come with most DSCR options) are better with a full doc loan.

If you are putting up cameras to monitor your tenants, such as putting a camera over the patio, that would probably be an invasion of privacy. 

Would love any tips/insight to help kickstart my journey or if you'd just like to meet up for an IRL/virtual coffee. 

@Bruce Reeves Since this will be an owner occupied property you have to make sure they have the ability to repay (ATR). 

Cool beans @Luis Vázquez.