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One of the concerns with real estate is liquidity and knowing when to sell so that you have access to liquidity when you need it.
Competition with friends, news of potential appreciation, emotional attachment can delay the decision to sell a property. However, focus on the need and that will help you decide when to sell it.
Remember that turning real estate into liquidity to fund goals like education takes time. Plan accordingly.
Purchasing decisions are often clouded by emotions and selling decisions can be hampered by attachments.