To sell or to rent that is the question!

[Riccardo Dux]

Im in a unique situation i bought a 2 family house about 6 years ago and it has been my bread and butter for much of that time. It has been paying its own mortgage as well as the mortgage on my single family home that i currently live in.  I bought it in the new york market at 550,000 and currently its worth about 900,000 to 950,000 in this hot market. I was put in a rough situation where both my tenants decided to move at the same time my next door neighbours are a consistant issue with being dirty, and being drug users. I find myself wanting to sell and take the large equity amount into another muti family property, but just as im most likey going to get top dollar the new property i buy will probably command top dollar as well.

I guess my question is being that i lived there for about 4 year im being told i wouldnt have to pay much taxes unless i net over 500,000 jointly with my wife. I am looking at about a 370,000 to 425,000 profit if i sell, but should i hold to my money maker on paper and continue to struggle with bills and issues eith tenants and neighbors or do i sell and try for a all cash deal like a foreclosure and net ecen more in rent? 

Any advice guys

[Jordan Grimstad]

I'm confused - are your options 1) sell and make a sizable profit or 2) hold and lose money/struggle to turn a profit? Is there an option 3 (hold and turn it back into a profitable investment in a reasonable amount of time)?

If option 3 isn't on the table...not sure why option 2 would ever be the one you pick. You could do a 1031 exchange and get into a more premium property and handle the tax situation as well.