I think the accumulation of rolling pin dents on my forehead after spending that much time training (away from Michiko) would definitely cause the pain to increase over time.
Seriously, though, it would depend. For an ultra runner, it might not be such a huge thing. If one is accustomed to exertions over the same amount or greater of hours as it would take to complete successive Skylines, then it might not be that bad.
The proper question might therefore be, "what's it to you?" In other words, how hard is Skyline for you? If you go up and it's no big deal and you feel fine the next day, then maybe the sucessive trips wouldn't be that bad. On the other hand, if Skyline is something you build up to, train extensively for, and you're really spent afterwards for several days, then doing it repeatedly is probably not even an option. I suppose that there would be a continuum between those two examples.
In general, even for the fittest, there would have to be a decrease in performance over time and an increase in suffering.
I think you'd have to determine for yourself just how taxing Skyline is for you. If it's not a big deal, just part of your regular training, then successive tries in one day or on contiguous days might be an option. You might want to consider, though, the possibility of "bonking" on a second or third attempt. The Rick K's of this world not withstanding, I think everyone has his or her limits. If that limit were reached in the middle of Skyline, that might be very very bad. Unlike a marathon, there's no nearby aid station. I think Skyline's inaccesibility is something to throw into the mix as you consider challenging yourself.
As for me personally getting back on the trail, I probably won't be doing anything too ambitious any time soon. I've got quite a "honey do" list, and I'm really out of shape having neglected regular excercise during the last month or two leading up to the wedding. I'm also suffering from some kind of hip inflammation, but hopefully that's temporary. I'm going to do some hiking this weekend in the SGW and see how that goes. Maybe Skyline in the fall...