As a result when the brokerage acts as the listing and selling brokerage  it saves both home sellers and buyers money.

Not too worry you will have plenty of people selling the dream to you.  

Even with multiple units, with current interest rates and a competitive market (prices have continued to rise even with higher interest rates) think the Madison market is a stronger long term ownership strategy, where the bulk of your return will come when you sell from appreciation in rents and property value. 

He is selling his house and the "home inspector "  says the deck wasnt built to code .

If you can hold on till first part of January the showings and everything else should pickup.This would be my action items: 1. hire a new agent that can sell the place, and get you numbers are rent and selling and sell the place. 2. be honest on the numbers you can get on an ARV so that you can sell it 3. start to get the conversation started with a couple lenders on what these numbers on refi would look like for you and this property 4. my suggestion would be to refi/rent before selling at a loss because if numbers work you can hold for a couple years then sell, but this is dependent on your cash position and liquidity of your situation. 

Perhaps you want to sell ownership interest.

It is solid to look at deals that are off-market and know that the ability to buy it at a price and either hold it or sell it will be coming with less competition on the purchase and more upside.  

Or stay a second year and sell tax free. 

Have you gotten out of the original hard money loan or still paying the double digit interest cost?

However, these costs can often be added to your property's basis, which helps reduce capital gains tax when you sell the home.Once the property is officially a short-term rental, subsequent repairs and maintenance would likely qualify as deductible expenses.