Yeah, not exactly the best location when it comes to the IC.

For a first-time trip I would recommend staying somewhere close or on Orchard Road (think of the Marriott or Meritus Mandarin Orchard as good examples location-wise), so the Hyatt would make a great choice here. As would the Hilton even though to go eastwards along Orchard you will always have to navigate the underground passage as the street-level pedestrian crossing is no longer available.

Do any of the hotel chains where you have status give free lounge access? If so this might be a key factor to consider.

As far as food goes I think you can easily skip Geyland and focus on eating more centrally.