Do you prefer to save up a war chest first before investing? Or invest with whatever you have in hand first?

No, add reguarly, do cost averaging.

We surely cannot time the markets, so much hassle...

Just take the 'boring' passive indexing ETF train,

let the winners run, do not listen to market noise,

avoid mutual funds, don't need to check ETF prices/developments often.

boring but successful in the past. no epinephrine mostly ...

Personally, what I like to do is to dollar cost average into the stock I want to buy. When there’s a sudden drop in price due to negative news and If I believe that the price will recover, I may put more money on my next purchase.

I don’t recommend investing everything in one shot as it is risky. But if you like to put large sums and not dollar cost average, maybe you can split it into 2 or 3 purchases at the support levels.

I definitely prefer to save up and only deploy my capital when an opportunity arises. Just like Warren Buffett chooses to sit on his cash pile (like right now) when markets are overvalued, you don't have to feel compelled to invest just because you have money in hand.

Assuming you are young, and with no dependents with an active life, do consider to buy personal accident insurance and top up your Medishield Life plan to an Integrated Health Shield plan (if you like private hospital treatment). Frankly, I believe that Singapore's public health system is really good and a Medishield Life plan is good enough, subject to personal ward preferences. Apart from personal accident, you should consider critical illness or term life - if you think you will start a family. This is to future proof your ability to provide for dependents - because starting term life insurance (not whole life) and critical illness at a young age is cheaper.

Apart from protecting your future, set aside emergency funds of 3-6 months income - depending on your lifestyle. With technology affecting job roles, you should be prepared for future changes. After that, you can consider investing. But there is no need to build a "war chest" as there is no end to the human perceived size anyway. Just start with what is available and keep investing to smooth out the ups and downs of markets. Stay focused and pick your risk appetite carefully. Fix a time horizon of at least one to three years. Any shorter, and you will be no different from a trader, speculator or gambler!

Singapore is fortunate to have digital investment services offering low fees and low investment entry. So check them out.

All the best!