Most advice I've heard is just to approach them after the sale, which in my mind is too late.

Of course there are sales skills . 

Question 2- could I split the sale over two years to help?

Hello BP Community,We’re under contract to sell our primary home in Indiana, and I could really use some advice on tax strategies—specifically, a Deferred Sales Trust (DST).Here are the key details:Purchased in 2010 for $499KUnder contract to sell for $2.499M (closing scheduled for December 2, 2025)Current mortgage balance: $94KThis leaves us facing a sizable potential tax burden.From my research, a Deferred Sales Trust seems like the only option to mitigate the tax hit.

Hello BP Community,We’re under contract to sell our primary home in Indiana, and I could really use some advice on tax strategies—specifically, a Deferred Sales Trust (DST).Here are the key details:Purchased in 2010 for $499KUnder contract to sell for $2.499M (closing scheduled for December 2, 2025)Current mortgage balance: $94KThis leaves us facing a sizable potential tax burden.From my research, a Deferred Sales Trust seems like the only option to mitigate the tax hit.

If this loan is in California, there's a 99.9% chance it's unenforceable with CA's new Jr Lien law, which is likely why the note holder is trying to unload it before the borrower stops paying and the note becomes worthless.- borrowers are already in distressI wouldnt go anywhere near this, especially because I do not and will not conduct business in CA (I see you're based in CA).

In selling sub to you want to obtain a price 10 - 20% over true market value, and sell to the buyer with the best chance of fulfilling the contract.  

@Heidi ChristensenDue on Sale is dangerous especially now! 

I'd look to work with a cpa to see what your basis in the property is including capital improvements and then put together an estimated sales price.

I have a vacant residential lot for sale near uptown Charlotte. 0.17 acre. 50' X152' pretty open flat lot.