Thanks guys. I tried to answer the questions in a way that made the article at least as much about highpointing as it was about myself. Been getting positive feedback.
In answer to Mr. Eagan's questions, there are probably in the ballpark of 10 highpoints that are significantly more difficult than what you find on the peakbagging lists in our area. There are basically five HPs that require roped travel. Denali, Rainier, Hood, Gannett and Granite. The standard route on Granite Peak, Montana also requires vertical rock climbing. The less-travelled SW couloir route on Granite is solid Class 4 but doesn't go vertical. Beyond that, Borah Peak, Idaho is a sporting Class 3 route, King's Peak, Utah takes you deep into the wildnerness and Boundary Peak, Nevada has a lot of scree and requires some pretty good route-finding skills. Mount Whitney, California also requires at least 6,700 feet (IIRC) of vertical gain by any route. So, what, I guess that's 9. The rest are day hikes or drive-bys.
As for altitude-related issues, I started having my doctor prescribe Diamox each year at my yearly physical and I found it enormously helpful although I used it in small doses. As needed, so to speak. The side effects are annoying. I would also always spend at least a day or two above 5K or so before attempting a western summit.