Need Advice on Structuring a Commercial Building Transaction to Minimize Tax Liabilit

[Matt Chandler]

Hello fellow real estate investors,

I'm working on a unique deal involving a commercial building that's been in a seller's family for generations. I'm looking for guidance on how to structure the transaction to reduce tax implications for both the seller and myself. Here are the key points:

Building is currently owned by an LLC, owned by the mother, who cannot manage it due to medical conditions. I've been assisting the financial POA, the owner's daughter on the deal and have an agreement(handshake and oral) at the moment and need help structuring the deal in the best way.

Goals:

1. Sell the building - I have a potential buyer in place for a premium. 

2. Pay off a $386k bank loan.

3. Reimburse the daughter $40k (she's covered loan interest, taxes, insurance, and maintenance)

4. Cover $150k in long-term care for the mom (either lump sum or 24 monthly payments).

I have an agreement in place to purchase at the above amounts and might assign the contract to a new buyer at a premium.

I need advice on:

1. Structuring this deal to prevent a large tax hit for the seller. 

2. Understanding the cost basis implications for taxes. I am working to get this information from their current accountant. I'm assuming the minimum cost basis would be the loan payoff, the $40k contribution from the daughter, and closing costs. They have owned the building for a long time so I am guessing the building is depreciated out but shouldn't the above referenced cost still be considered to be the cost basis? 

3. Minimizing potential tax liabilities, especially regarding the $150k for long-term care. I am assuming this part of the sale would be taxable via long term capital gains and was wondering if there is a way to creatively structure the deal to minimize this? There is room in the deal on my side to help on this as well if needed. 

4. Suggestions on my end for how to structure the deal to minimize tax liability – I plan to assign the contract for a fee at closing. Would this be Active income for me? I currently have a NOL(Net operating loss) from previous years return. To my understanding long and short term capital gains can NOT be offset by my NOL. Would assigning the contract for a fee be considered Active income that I can offset with my NOL? 

Also is creating a contract with my real estate company(currently an S-Corp) with the seller and assigning it to the buyer for a fee at closing the best way to structure the deal given the components of the deal? 

Thank you in advance for any insights or experience you can share!