As much as possible avoid financial/material transactions with family/friend

This is purely based on my own experience. I had some really bad experiences when I tried to do financial/material transactions with family or friends. A few examples to set the context:

1. Selling your home/car to a good friend

2. Buying car from a family member

3. Helping a friend buy real-estate through your contacts and then the real estate tanks

4. Giving a loan to a friend and later end up following multiple times to get the money back

In all these scenarios, I ended up in emotionally challenging situations. One of my friend stopped talking with me. Another changed the way he interacted with me and I could sense the bitterness. I tried to fix these relationships, but was not successful.

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Let me share an example. A friend trusted me blindly and bought real estate at the same place that I bought. The projection was, the price will grow exponentially. But the opposite happened. My friend took a personal loan from bank, paid high interest rates and the property value did not even make up for the interest paid..

Long story short, be very careful when you are engaging in financial transactions with friends and family. My personal recommendation is to avoid this altogether.