There are many financial products, but the 'least intimidating' way to start off investing in stocks is to buy those listed on the
SGX. Of course every investment has risks and you decide how much risk you can stomach. To me this is least intimidating because the process is clear cut and the chances of you being 'cheated' is very low.
1. Take the
sgx modules necessary to open a CDP account.
2. Open an account with your chosen brokerage firm (DBS vickers,
UOB, etc)
3. Buy your stocks via your brokerage firm app.
4. If you are keeping for long term, the stocks must be delivered to your CDP within 3 days and they are under your name.
5. Profit / Loss depends on when you sell, and the only fees you pay are to your broker,
GST and clearing fees to
SGX.
This is a good time to think about buying stocks because most of them have lost a 25 to 30% of their pre-covid value. People say the 'safer' blue-chip stocks are majority owned by Temasek, like Singtel. Not saying that just because there is Temasek, your investment is totally safe. If for some reason they decide to bail and sell off, the value will likely plunge. However, if there is one thing I have learnt from observation, bad times dont last forever.
Which leads me to your parents losing a lot and you are afraid of 'playing stocks'. My take on why many people say or have parents who 'lost a lot' is they probably bought expecting prices to go up, but panicked and sold off when the stock prices plunged in times of crises.
A more rational response would be to evaluate whether the company can weather the crisis and grow in future and if you can hold off cashing out for a few years. Using Singtel as an example, chances of it collapsing are very slim and yes there are competitors, but even if its price plunges for the whole of this year and longer, I am confident it would recover. And it did indeed recover from its ~ $3.50 plunge to ~ $2.50 in 2008, although over the next decade.
To be frank though, there is no way you can live off dividends investing in
SGX stocks unless you have a lot of money lying around, which from your post seems unlikely.