In my opinion the major setbacks you are going to hit will be:- Size of your lot (DCRA typically requires at least 900sf per unit you want to build- but there are some ways around this-- this is not 900sf of living space, but land)- Your Zoning (if it's R-4 then you're in pretty good shape with regards to being able to build a pop up and as John said if there are properties in your neighborhood with a popup, which Columbia heights has an abundance of, then Precedence really helps)- Extending the back of the house will be difficult as would underpinning the basement to deepen it- not so much because of zoning requirements, but more from a cost and technical implication as it's always a pain when you mess with the foundation of these old houses.If you want to talk about it more in-depth shoot me a message and I'd be more than happy to discuss further

I may need a more accurate repair estimate, and I need to get the exact payoff amount (which i'm having a hard time getting since i'm not authorized to talk to the bank regarding the loan and the guy who can authorize me is a pain to reach).Anyways i've spoken with his old attorneys and they dont have POA's but I did get a call from his mother who was corresponding on his behalf.

Fence maintenance, insurance, lawsuits, code violations, squatters, floods, dirt, mud, trash, illegal dumpers, property infringers ...what a pain:)

My husband works a transient job so we have been able to turn personals into rentals.Getting started young is painful.

Not impossible to do but more pain in the *** than it's worth in my life.A straight and dry Option is better.

As you can imagine, tax implications are a pain and I have to figure out some of the details before I get started.

Every time I spread mud over a section of a wall it feels as though the house is sighing in relief and gratefulness for the healing and soothing salve I am applying.  

I truly feel your pain. 

Value is a pain in the butt to determine on properties.  

I remember during my college days we had tapestry over the entire ceiling, area rugs, dressers up against the wall, book shelves and milk crates of records and books, it's a real pain to do a thorough inspection.