House hacking seems like the best strategy for me.My goal is to purchase a single-family home in Maryland, D.C, (from lurking I've heard D.C was terrible for investing) or Virginia with multiple rooms where I'm making monthly payments similar to what I pay in rent and other charges ($2000-$2500).

For Conventional, you can only use 75% of the gross rent until you have Sched E history for the rental for a net rental income analysis. 

Then they'll charge an additional $2,400 for filing tax returns. 

If you update to max number of conventional units, you will be able to add an ADU for each conventional unit

And how do I roll this into a cheaper mortgage (my dti would be too bad for another conventional).Maybe a lender would be able to consider the electric "working" with the proper inspection?

I do not have a traditional W2 job so I can't pursue the typical conventional loan or a FHA since I don't have income (hence the DSCR route).However, I've seen that most DSCR lenders do not lend if the loan amount is less than $100K.

Financing: I’m planning to use conventional financing for this purchase.

Also, I am guessing that due to the state of the house, it would not qualify for a conventional loan?

Quote from @Aaron Wolman: Yes, these charges are fair.

You could also use a Fannie May Home style renovation loan which a conventional loan and require 5% down vs.