
From the looks of your setup, I'd say probably. The lift and bigger tires would benefit from a stronger transmission like a T176.
Do you know what your axle gearing is? How fast do you typically drive? You can use a site like grimjeeper to determine engine speeds for your tire, gear, and transmission setup and see if you're OK with a 4spd or if you need an overdrive 5spd, and at the same time make sure your gearing is appropriate for your tire size. For all we know you're running 35s with a 2.73 gearing and no tranny would be able to keep up with that.
You will need new driveshafts with the T176, which'll run another $300 or so + ujoints and straps. You'll have to look out for a T176 that comes with an adapter to the D300, too. Some people try to sell them without the adapter and then you have to hunt for it. While the T176 is shorter than the T5 by a few inches, you'll still have to see if you'll need a double cardan setup by measuring your incline angle from your rear diff to your rear output shaft on your transfer case.
Before you dive too far in, you might just consider a near-complete drivetrain swap to get rid of that 4cyl...maybe a YJ 4.0 with fuel injection and a AX15 behind it mated to the D300. No matter what, give this a lot of thought so you aren't wasting time and money on a short-term fix.