What bOLsAK3 said, x2.
If you do happen to tear the boot on your front DS, the only immediate impact will likely be a bunch of cursing from you. Your JK should continue to drive fine for quite awhile after that, so why replace it for a condition that you may never encounter?
lax71vcu, I've got the same JK setup as you, and I've been wheeling it with a TeraFlex 2.5" coil lift with no problems.
Since you've got an automatic, you've got a transmission skid that only autos get. After just about any amount of lift, when you're flexing, the DS will make contact with this skid. So if you plan on doing a lift, plan on either losing this skid, or cutting it so that it's more DS friendly.
I replaced mine with the Rock Hard 4x4 skid. In addition to the trans, it also covers the oil pan and cat converter. I've had no problems with rubbing with this skid.
STUPIDLY, I've had this skid off for about a month (it was covering and area I wanted to work on). I got a chance to do some unexpected wheeling a week or two ago, and didn't want to take the time to put this skid back on, so I put the stock skid back on. I didn't plan on doing much flexing where I was going, so I thought I'd be fine. Wrong -- ripped the DS boot about 10 minutes into the event.