I've been thinking to start a regular savings plan with DBS. Is now a good time to go in?

The regular savings plan will result in a fixed amount of money invested every month via a dollar cost averaging (DCA) method. This strategy performs better in a downward trending market because it averages out the price of your shares, and you will reap the benefits when the market starts to recover. In the flip side, a lump sum investment works best in an upward trending market, especially if you can time the market perfectly and catch the bottom. So if you're bearish about the market, DCA generally serves as a good strategy to adopt.

You also mentioned that you wanted to hit a higher interest rate, would you be able to share if the rationale is to hit the $50k cap as well?​​​

The fact you had to query whether it is a good time to enter now, means next time you will def will ask other people's advice when it is a good time to exit. Independence of thought (whether in hindsight turn out to be right/wrong) is paramount to sound investing.

You should probably first picked up some value investing books to improve your financial literacy skills before embarking on your investing journey.

As long the stock market is open, opportunities will always be there, its ok to miss out once in a while. BUT once you suffered a permanent loss, you can kiss your hard-earned monies goodbye