It all starts with filling in the nomination form correctly. You will need to find a commissioner of oaths and a couple of ascentors. Ascentors must live in the estate you are competing in.
Once the administrative matters are done, you should start campaigning. You will need to print your manifesto for the estate and voting cards that help nudge voters the right way. Be mindful that the messages must be written in 4 national languages. Tamil is really tough.
You will also need posters on wooden boards. You must be able to find volunteers to distribute the brochures and voting cards. Some volunteers should also help you put up the flags. Your election agent must make sure all these collateral are licensed and approved by the elections department.
You will also need help to put up at least 500 posters for one SMC or part of a GRC. Getting volunteers is a tough exercise because you may not be able to afford to pay them. As a candidate, you probably have used up most of your money on the deposit (more than 10k SGD) and on the collateral.
If you belong to a small party, your party may not be featured on the political broadcast. You will also have less opportunity to speak at rallies. You will also have to pay for the stage during your rally. The sound system will not come cheap too. Beyond payment, you will also have to find good and credible speakers to help you win votes.
Before the polling day, you will need to find dozen of polling agents who will station themselves at the polling centre. You will need to appoint an EA (this happens right at the start) to help brief them on relevant procedures. You will need some counting agents to help monitor the counting process. Both polling and counting agents need to be sworn in by a commissioner of oaths. This can cost up to $20 per person.
Things get messy on the polling day. You and your election agent should make sure your polling agents and counting agents have sufficient food. The polling hours can be very long.
No matter the outcome, you will need to speak to the media that day, to concede or to thank supporters for the victory.