1. I booked my last flight to Kauai nonstop, through the portal on Hawaiian Air. Hawaiian is bookable through the portal.
2. You can transfer the points directly to Southwest, and that makes the value of the 100K more like $1,750, instead of the $1,500 through the portal.
3. The UR Portal is based on cash prices.
If I could even get a single seat on Hawaiian or Alaska with 40K points, it's hard to do, RT would be 80K points, which I have transferred from SPG in the past. My SPG gets the 2X on MF's. That is a $40K spend at 2X Starwood fees. I would love to be able to book two of those seats, but they don't allow for two award seats on flight, initially. I cannot wait for them to open another award seat to book, so I have to pay cash for one seat. Kind of annoying. With timeshares being weekends, I need to fly weekends to Maui. There is huge competition for those seats, especially during whale season.
The realization of the impossibility to get two seats from Denver to Maui with award miles made me rethink my plan. I started looking at First Class seats from the coast, finding the cheapest ones, then booking with the UR portal, way ahead of time, to get the low-cost seats. Then we fly Southwest to the coast, spend a night on the way there and on the way back, all with points. It's been working great. But honestly, I miss the Alaska companion code, which worked for First Class seats to/from Denver wonderfully. Now it's just economy, and I am so spoiled.
I agree with you that it is getting harder to get reasonable First Class award seats to Hawaii. I put in LAS - HNL and the portal did not provide me with any Hawaiian Airlines option.