Knowing when to sell and when to hold?

[Vincent Plant]

I have both sides of a twin that I have owned for about 3 years now. They are rough to say the least. In a rough area, in rough condition, low income tenants that don't take good care of the property. 

All in all it's been a pretty good run with them. They cash flow nicely (when the tenants pay on time). I got a great deal on them. My mortgage is low, the maintenance has been much more manageable than I expected, and in my 3 years of ownership they have appreciated considerably even with all the negative factors. 

I had the boro go through them recently and they are in really bad shape. I know I am going to be facing a lot of large expenses. I know the way the market sits I can unload them as-is and make a nice profit on them. But do I want to sell off 2 homes? I have always heard the saying never sell an asset when building wealth. And what am I to do with the proceeds? I could never buy homes now for the price I paid for these. 

Should I grind through and try to maintain/fix these places up? Or sell off my class D assets to try and upgrade to better properties? 

[Joe Villeneuve]

Why is Kenny Rodgers singing in my head as I'm writing this?

It's all about math here, and since you have provided no number$ the answer you're looking for is impossible to give.  However, keep this in mind, the longer you hold a property, and the larger the percentage of equity grows in that property, the more money you are losing because that equity is buying less and less in property value per dollar of equity.  Also, all the equity that is dying more and more as it grows, could (should) be buying more than just the 2 properties...which will actually be increasing your cash flow too.