Thanks! I did call in, the agent said "wait please; we almost always have R-availibility on that route." Couple minutes later, I was upgraded both segments (including the RJ to CLE); one RPU taken.

With her statement about R availability, I almost decided to take my chances on the CPUs; but with the 6+ hr flight, I won't have to "worry" about getting the upgrade. And BTW, the next day, this flight ANC-ORD was then showing R2 (23 days to go); 5 of 20 seats shown as "available" on seat map.