I said all that to say this its several folk in both classes that have spent money and time and will get nothing out of it .

What has a lot of folks spooked is that simply doing a 1031 exchange is an attempt to avoid tax. 

To pay for this, I used a heloc on my current home.

I’ve had people who signed up for 6 months and stayed 5+ years, paying increasing rental rates.

It seemed like most the folks you have on staff are CPA or other, but no specific legal experts.

Plus I need to leave my folks' place at some point lol.

Use that loan to pay the back taxes and get things under control.

Quote from @Surya S Kumaresan: Hello Folks,Hope 2025 is off to a great start for you all!

We're trying to decide whether or not to pay it off or save to buy another property. 

Imagine you make $100k and you are affected by 3 tax brackets.0-33k =-33K 0%33,001-66k 10%66,001 - 100k 20%You can take $100k in deductions this year and pay zero taxes, for one year and then $10,100 for for 2 years  ($20,200 total)You can take 67k in deductions this year and pay zero taxes for a year, take 33k the second year and pay $6,800 year two and $10,100 year 3. ($16,900 total)You can take 33k each year and pay $3,300 in taxes all 3 years. ($9,900 total)Obviously this is simplified but unless you expect to make much less and be in a lower tax bracket in the future those deductions could come in handy.