Probably will do the transit hotel and a little breakfast so would be looking for a flight around 10am or later.
It's all much of a muchness for a 50min flight, although if you prefer a wide body, SQ has one at 8.30am, and HY at 9.10am. Then it's A320s/737s doing the rounds for the rest of the morning.
WY has an A330 departing at 5.15am if you ever want to consider not using the transit hotel at all.
Personally, I would just take whichever is cheapest. This route almost has a shuttle bus feel to it.