Will a bank see the same value that I do and be willing l do a DSCR loan based on LTR and STR on the same property?

If my lease did not have this as the tenant responsibility, I would reimburse you based on those pictures.  

Passive income is something talked about, but the majority of real estate investing is far from passive and what is called passive has payments for the passivity (management).Your why is strong, to provide generational wealth for your family and likely achieve time freedom long-term, that's awesome.

You can't do that anymore... not in an area as strong as this one.

DC is one of the lowest cap rates in the country.If you have a long time horizon, and have patience, with the areas strong rent growth you can end up with more cash flow here than a high cap rate market.

However, I can tell you this based on 40+ years having purchased over 150 properties, financed over 500, and brokered too many to count.  

I would like to know the following based on your knowledge of the area.1.

These properties were not distressed quite the opposite.. but they had 100k to 3 to 5 million of standing Timber on them that if we could purchase our Timber deed we could turn those trees to cash within 90 days..PS I had created a hand made custom data base of properties  10 acres or more not corporately owned that Aerial Photogramy show Standing Timber of an Age we deemed Merchantable. 

Once you feel you've built a strong team with your first property and have solid systems in place, I would then start buying more aggressively and taking on bigger projects.I suggest reading this BP article on the core 4.https://www.biggerpockets.com/blog/core-four-real-estate-team

We are based here in Chicago and have GC business, for reference.