If you want to see Raffles, you should be able to get a cheaper drink outside in a courtyard (where IME there's sometimes decent live music). Avoid the Long Bar (where the Singapore Sling was supposedly invented) as it's an overcrowded tourist trap. OTOH, going to the Writers' Bar gives you the opportunity to go inside to see the lobby; be sure to look up to as it's basically an atrium.

For tourism, the Bugis area is a much better location than Orchard Road.