Certainly, the beauty is in the eye of the beholder. Being in FL, there are always specials and discounts on cruises, even in peak season like summer. Peak Season normally starts about the last 2 weeks of June if I recall (around 17th some years) and since our kids are out of school in May, we've normally cruised early June.
I don't think comparing Disney to other cruise lines is quite the same as the on site/off site comparision. There are no theme parks to be denied early entry into. Many actually prefer some of the other cruise lines at the same price, for various reasons, even for some that have been on
DCL. I haven't been on the Disney ships but have looked at the info fairly extensively, looked at ratings and objective reviews and have been on RCCL several times. I couldn't justify a significant premium for the DCL cruise, others obviously can. That's not to say I wouldn't love to go on one, just not that I'm willing to pay an extra $1000-1500 for a family of four, whether in points or dollars.
As for the break point on using points, I'd put it at about $8 pp for me. I bought OKW resale so it might be higher for others. I figure I could rent at $10 pp but there is a hassle and risk factor in doing so and therefore give an adjustment for a sure thing. Good luck and enjoy and possibly some day we can do the DCL.