Like kind exchange of 2 properties for 1

[David Floyd]

Im trying to sell two investment SFH in Florida on the coast that are only returning about 5% (net income/property value). Both are totally paid off and Im looking to do a simultaneous like kind exchange for a property in a ski town in Colorado. We are currently looking at Telluride and Crested Butte. The plan is to sell either one or both and buy either a lot and build or a preexisting SFH. From what I have been told there are two feasible ways to do this:

• Option 1: Sell Property #1 and within 45 calendar days, sell Property #2. This will allow both properties to be part of the same exchange. You would still need to close on the property by the 180th calendar day that you sold Property #1. 

• Option 2: Sell Property #1 and Property #2 outside of the 45 Day ID window. ID the replacement property within the first 45 calendars of Property #1’s sale. The key here would be that you could not close on the replacement property until both Property #1 and Property #2 have sold. You would have 180 calendar days to close on the replacement property after Property #1 was sold. 

The plan would be to use this replacement property as an investment and then turn it into a second home or a primary residence after we sell our current home tax free.  

Getting both properties to close within that time frame seems difficult so we may just end up selling one, buying a lot and building ourselves.  Any advice from the 1031 experts?