Since a 1031 exchange is time sensitive I can't risk not selling all three together.  

This particular strategy was personally told to me by Jimmy while we were driving from Phoenix to Las Vegas in the early 1980s to attend a real estate exchangers conference and exchange session.   

Here is a list of my suggestions:1) 1031 exchange your current condo & buy one or two small multi family (2-4 units) properties that have a better cash flow.

That is like 1031 Exchanges that you can do with a good Title Company who has that Department.

Only one filer can claim that property if you read all the requirements. 1031 exchange would require all of the partners to agree on moving the proceeds to a new property and deferring their gain.

I also know that doing a 1031 exchange will enable us to carry all of the proceeds from the sale as a deposit on a new property.   

@Patrick Irish based on what you say, the Sec 121 Exclusion and the 1031 Exchange both seem like they'd be good options for you to defer capital gains on sale of the townhouse.Sec 121 Exclusion has 3 requirements: First, Determine whether any of the automatic disqualifications apply (acquired property through 1031 exchange in last 5 years, or subject to Expat taxes)Next, meet the ownership requirement -> you owned the home for at least 24 months (2 years) out of the last 5 years leading up to the date of sale (date of the closing)Finally, meet the residence requirement -> owned the home and used it as your residence for at least 24 months (or 730 days) of the previous 5 yearsThere is no “Wiggle Room” but there is a Sec 121 “partial exclusion” for people like you that missed the residence requirement by a few months.

A 1031 exchange, an installment sale, and a Delaware Statutory Trust (DST) are just a few.

Tough to beat this answer from @Michael PlaksYou can also check out these two recent posts that walk through Section 121 Exclusion and 1031 Exchange guidelines and strategyHow Section 121 Exclusion and 1031 Exchange works: https://www.biggerpockets.com/forums/51/topics/1195208-1031-and-sec-121-experts-want-to-sell-rental-but-tax-worried What not to do if you don't meet the requirements for Section 121 Exclusion and 1031 Exchange:  https://www.biggerpockets.com/forums/51/topics/1195383-5k-for-cap-gains-tax-opinion-quote-that-reasonable ...

with the intention of doing a 1031 exchange on that property and the goal to utilize Brandon Turner's "stack" method to dump the proceeds into a bigger property with more units in a similar market within Worcester county.