What I am probably going to do is just drill two holes in the a-pillar, and insert anchors that my handle can then screw into.
Only problem I see (at least on my '99) is that the a-pillar plastic cover on the passenger side is flat around the area of the handle. On the driverside, it is rounded all the way (because there is no handle), so it will look different then the passenger side. Here are 2 pics from my gallery that illustrate what I mean. Look at the a-pillar plastic covers on the passenger side versus the driver side:
Passenger Side A-Pillar
Drivers Side A-Pillar
It's not really a big issue, but I like to make everything look as close to stock as possible.
I'll take some pics when I do mine. Should be pretty soon as I am going to be doing the lift soon, and my wife will be on my ass about the grab handle if she needs to drive the pickup.
Do you think there are any issues with drilling anchor holes in the a-pillar? Will that weaken it significantly?