Keep the 8.25, or put in the 8.8, it really doesnt matter. Either way you will be reagearing it, both have drums which is kinda lame. As far as strength, on 33s you will be more than fine on either. Keep in mind the 8.8 has more aftermarket support, BUT it will require you fab up brackets to install it.
Since your going with 33s, one option would be sell the 8.25 and 8.8 and spend $200 on a 8.8 with disks and 4.10s. They are everywhere, and you'll have disk breaks also, more aftermarket support, and a free re-gearing. Then get a d30 fron the junkyard from a 4 cyl taht has 4.10s. Then you save about $1000-$1600 on gearing (depending on where you go).
There are ups and downs of each option, but i would pass on 44s in this situation. Also one thing to point out is that your 8.25 has 27 spline shafts, im not sure how they stack up to the 29 spline version in terms of toughness. 8.8 will have 31 spline if you get the explorer ones.
Where did your drummed 88 come from? If its full size skip it, also toss it if its got the 28 spline shafts.