Legitimizing yourself is key because owners many times have either been burned by owner financing before or have had really amateur investors approach them with it so they will be extremely cautious about it. 

Market value are extremely low on most properties which will result in a huge spike in property taxes.

Joe Schmoe62 years old$4,300 a month gross incomePlans on retiring in 3 years, wants to downsize to a more affordable unit in preparation.All seems great to me so far, but upon running his information (I used "MyRental" for the credit/background check), found that he has an extremely limited credit history?

It's extremely rare that two applicants are equal.

Asking for a friend: I have an extremely obnoxious neighbor above me.

They were just extremely efficient in a geographic location where the cost of labor and the cost of living is substantially lower. 

I bought the property and invested a little bit of money in it for personal gains, life happened I sold said property and it was then, I realized the ease and extreme excitement I felt buying and selling real estate.

I would approach the tenant extremely professionally and be upfront with them about the situation and give them a chance to explain what happened.

Hi @Mateen Qureshi and welcome to the forums, being a buy and hold investor in DC can be profitable but you may run into cash flow issues as the DC market is extremely tight.

Idea was to secure favorable mortgage before rising rates while also leveraging extremely competitive rental market.What made you interested in investing in this type of deal?