Property investments don’t always go smoothly, but it’s often the success stories you hear about. In reality, not everyone manages to sell for a record gain after five years and upgrade; and not every rental property ends up being worth its initial capital. We spoke to some property investors about their biggest regrets and the lessons they learned in the process: Table Of Contents

• 1. Buying a property while under-capitalised
• 2. Trying to wait out the “temporary” cooling measures
• 3. Buying old walk-ups for rental 
• 4. Investing with someone who has entirely different aims

1. Buying a property while under-capitalised

Our reader TT says he dived into the property market before he was properly capitalised, and learned a painful lesson from a forced sale: “In 2007 I became fascinated with the property market after one of my old school friends made his first million in property investment,” TT says, “I was so eager to follow suit that I bought a 920+ sq. ft. unit  ...