All Forum Posts by: David Ashworth

I hold land personally with my wife that I am selling and at the same time I am purchasing my first str. The str will close before the land sells and then I would like to recast the loan to pay off a portion with the land proceeds.  We are taking a cash out loan on my primary residence since the rate is over 1.25% lower. We will use proceeds from the str to pay the note but may be missing some tax benefits with this structure. 

- The land was homesteaded under the same parcel ID as our primary residence as it was next door and will be carved out at sale.
- We have lived in the house more than two years.  
- We will sell the land for about 2.5-3x what we paid.  
- The str will be purchased in an LLC

QUESTION: Is there a way to defer/avoid paying taxes on the gain since it's held personally as part of my primary residence and we have lived there greater than two years and the gain will be less than $500k or as a 1031 exchange investing into the STR LLC?

Thanks 

Hi all, buying my first STR and selling a piece of land I bought in 2021 for 4x to help reduce the note. I'll have this place more than 50% paid off and will see how the rental market fairs before adding leverage. The house itself will be paid off. Note is on my primary residence. Came to learn more about the right leverage to try and get my second STR shortly after as well maybe in the same market. Maybe northeast.