Can I 1031 exchange these 3 properties? Y/N?

[Rachel Hughes]

Property 1: Purchased as primary residence in Feb/2020. It is a SFH with an attached in-law suite.

Main house has been a short-term rental since March/2020.

In law suite was my primary residence from Feb/2020 - Feb/2021 (1 year).

Both units are now short-term rentals, so property is 100% for investment purposes now.

Property 2: Purchased as an investment property in May/2021. Has been a short-term rental ever since. 

Property 3: Purchased as a primary residence in Feb/2021. I lived here from Feb/2021 - October/2021 (8 mos.). Property has been a short-term rental since October/2021 (7 mos.). 

[Chad McMahan]

Quote from @Rachel Hughes:

Property 1: Purchased as primary residence in Feb/2020. It is a SFH with an attached in-law suite.

Main house has been a short-term rental since March/2020.

In law suite was my primary residence from Feb/2020 - Feb/2021 (1 year).

Both units are now short-term rentals, so property is 100% for investment purposes now.

Property 2: Purchased as an investment property in May/2021. Has been a short-term rental ever since. 

Property 3: Purchased as a primary residence in Feb/2021. I lived here from Feb/2021 - October/2021 (8 mos.). Property has been a short-term rental since October/2021 (7 mos.). 

1031 exchanges are extremely easy to screw up. The best advice anyone could give you, is get a consultation from a 1031 rep and do it right.