I am a local and have been on the High Roller three times to escort various visiting family members. I enjoy the ride because you hardly feel like you are moving. It is an ok view of the Vegas valley on one side and an amazing view of the strip on the other.
The best time to ride is at sunset. This way you get a day view half-way up and a night view on the way down. This of course requires some timing on your part.
Because it is an extremely expensive 30 minute ride, you'll want to time your visit with lower than normal crowds. Then you'll have the best opportunity to board a pod that is not being packed with too many tourist to enjoy the views.
They offer military and local discounts.