Between now and then you can really crunch the numbers on rent vs. costs and decide how much negative you can stomach....at worst you still decide to sell in the spring and maybe it's a $40K loss instead of your current estimate. 

This can protect your other investments should you have a loss in one.

Should I have a family member live there at a loss each month?

And then as part of the land business, I saw an opportunity to go into new construction in eastern tennessee area with the vision of building some to sell and building some to hold - to where I could replace all the equity I gave up when I sold about half of my rentals here in Illinois.So now I'm sitting on a hefty pile of cash.

It would be an improvement over paper as money, but there would be tremendous loss of privacy. 

@Kameren Powell I’ll try to save you from financial loss.

Does HOA have loss of income insurance or some fund to make up the losses until owners get property rehabbed or built?

This creates two loan payments ($100,000 of equity and $300,000 on the new mortgage).Key NumbersHome Equity Loan Interest Rate: 6%Mortgage Interest Rate: 7%Rental Income: $3,000 per monthExpenses (management, taxes, insurance, maintenance): $800 per monthIncome and ExpensesMonthly Rental Income: $3,000Monthly Expenses: $800Monthly Mortgage Payment: $2,000ExplanationThe investor earns $3,000 in rent each month.They pay $2,000 on the investment property mortgage and $800 on other expenses.This leaves $200 profit each month or $2,400 per year.However, you have to pay $6,000 interest on the equity borrowed.This leaves you with an annual loss of $3,600.This example shows that while the rental property generates positive monthly income, the interest cost of borrowing the initial $100,000 results in an overall annual loss.

Many people are suggesting to do a 1031 but have no idea what your gain / tax is(if any).Co-ops in the tri-state area 'normally' don't appreciate a crazy amount.The main reasons is the high monthly maintenance costs, over-leverage of the board, potential difficulty of buyers getting a mortgage and the approval process of the buyer.With that said, talk to your CPA to discuss what your gain / tax would be before thinking about a 1031 exchange.If your tax burden is low, don't bother with the 1031It may be possible that you have suspended passive losses to cover your tax burden.best of luck.

Meanwhile, my investors that bought a property from a REIT had a 60% paper loss from just purchasing the property.