Need some money, what should I sell?

[Ben McMahon]

So I am having a cashflow issue right now, and Im not sure what to do about it.  Without getting into the nitty gritty of why I need the money, I am planning on selling one or more properties.  I really don't want to sell anything because I worked hard to get these properties, and over the last few years I have only kept the ones that are solid.  It seems like a step backwards to sell anything because my longterm plan was to grow a large portfolio of properties.  

I have a lot of money tied up in some other projects, and I don't know when those are going to pan out.  I owe money to some people, some people owe me money, but its been tough lately.  So, the question.

Which property should I sell?  There are a few that are tied up with other investors, so they are off limits, but the ones that I plan on possibly selling are 4 different ones

1) Hot Corner - Single family that we renovated a few years ago in an almost exclusively commercially zoned area.  I can rezone and make into an office without many upgrades.  Its at an extremely busy intersection and can be used as small office or flex space.  Problem is that it would take months

2)Picket Fence - Perfect little 3 bedroom in quiet area.  Really good rental, and have had a solid tenant for a couple years.  Not amazing cashflow, has been almost maintenance free

3) Double up Duplex - Bought this sucker at the bottom of the market, and is worth twice what I paid for it.  Its got tons of upside because the whole area is currently getting new roads and a new bridge etc.  The place itself has good cashflow, but its an old building.  

4) First time Townhome - My first investment property I bought in 2010 and like the others has been a great property.  Its worth more than double what I bought it for, and I've always had good tenants.  It also has some sentimental value, although I am pretty good just looking at what makes sense.  

I realize there are a ton of variables here, but I have to do something.  So which one?

[Jerry W.]

@Ben McMahon, I would go with #2.  The one with the lowest cash flow.  Furthermore if it has not gone up in value as much as the others you will have less capital gains taxes.  it might be worth your time to check with your accountant on what your taxes would be depending on which property you sell.