@Nick Gee Your best bet to avoid or defer capital gains would be to use a 1031 Exchange to invest in a new property.

Roofs are expensive, but a house with a new roof and AC in 5 years is likely worth more than a house with those components in poor condition today.

You mentioned not raising rent in 16 years, so I am betting three things:1.

. - each unit is over occupied; one 2 bedroom has 8 occupants with beds in living room etc. lots of poor tenant improvements… extension cords coming out of windows, sheets on windows, etc-fairly nice area- property was mismanaged and is quite sloppy.

Best bet is to meet with someone face-to-face to explain your situation and see what they would be willing to do for you, I'd recommend researching and setting up meetings with a variety as it may take some time to find the right one.

Your best bet might be to use a personal loan or credit cards for the rehab.

Robert Kiyosaki’s “Rich Dad, Poor Dad” and “The Richest Man in Babylon” and man….

@Oscar Sanchez whenever I think about a purchase like that my mind floats back to Rich Dad Poor Dad and try to classify it as an asset or liability. 

It is the cheapest stuff you are going to find inside the beltway and long run that seems like a good bet to me. 

If you have not, great books to read are:• Rich Dad, Poor Dad• The Millionaire Next Door• Cash Flow Quadrant • Tax Free Wealth• Set For Life• Rental Property Investing• The Millionaire Real Estate Investor• The REAL Book of Real Estate• So Good They Can’t Ignore YouYou are more than welcome to reach out if you have any questions.