My cofounder at SparkRental, Deni Supplee, hosted a foreign exchange student to house hack when she was in her late 50s and early 60s.

Since we would be using the money in the same manner could we use a 1031 exchange to defer the gain income tax ?

I have a SFHs, duplexes and a 4-plex and would like to eventually sell the SFHs and 1031 exchange them into MFs.  

If I trade property I own in exchange for a property owned by a non-profit organization, what do I need to consider regarding taxes or anything else that could impact the transfer?

My wife, though she knew the area and went to college here, wasn't sure she wanted to move back, but she is loving it and happy to be away from the congestion of the Sillycon Valley.We started buying a condo for students in 2007 and just prior to COVID lockdown, sold it and 1031 exchanged it into two fourplexes. 

She is talking about paying off the delinquent taxes (in exchange for a lien) and then having the Sheriff sell the property at auction. 

I know the capital gains tax on investments shorter than 1 year have at least 35%+ tax.I try to tell people to beat the tax with volume, the 1031 exchange program can be a pain with their guidelines and process. 

@Brett Stec this is a tough one since the primary residence exemption won't apply to her and she won't be able to do a 1031 exchange since it isn't an investment property. 

Upon the sale of the condominium, the capital gains on Person C's sale would be calculated as follows:A. 33.33% of the sale price minus the original purchase price to account for the interest acquired via quit claim deed on July 7 2015.B. 16.66% of the sale price minus the stepped up fair market value on 11/17/2020 as capital gains for the 16.66% remainder interest acquired on 11/17/2020 from Person A.C. 50% of the sale price minus the stepped up fair market value on 01/17/2023 as capital gains for the 50% remainder interest acquired on 01/17/2023 from Person B.Total Capital gains would be the sum of items 3A, 3B and 3C above minus any allowed deductions, such as the home sale costs (closing, repairs and so on).As an individual owned rental property, upon sale the only way to avoid the capital gains would be to do a 1031 exchange and then hold the new property that is purchased for approximately 3 years before selling it. 

  - There are a lot of good folks on BP who have been in the game a long time and can vouch for different QIsAs for your DIY model: you can't do 99% of exchanges on your own, the IRS won't let you.