When to sell?

[Elizabeth Chevalier]

When do you know when to sell a property? I purchased a short-sale for $100K with $20K down three years ago.  I have a 30-year mortgage at 4.375%. I spent an additional $15K in repairs and rent the home as a vacation rental.  I've probably made about $50K net over the past three years  This year I will net $25K, but I have over $100K in equity in the house value only.  If I can find someone who wants a vacation rental I could sell the property for more. Should I cash-out of this investment and reinvest my money?  My one concern is that the cashflow of the vacation rental could decrease along with the home value if there is a recession or a housing downturn. So should I just cash-out while I am ahead?