This has been covered before on the forum so a search can get you more detail.
In a nutshell, you should test drive an off-road with and without KDSS to see what you prefer or can tolerate. I can't stand the on-road handling without KDSS, I can deal with the on-road manners with. I test drove both before buying.
In terms of TRD Pro, I agree with the earlier comment that it only makes sense vs. a TRD Off-Road Premium if you are going to run stock. Otherwise, you will throw away the suspension if you do a major suspension lift (not a spacer lift), which is the main benefit of the TRD Pro over the Off-Road, IMHO.
The Pro does have some minor other improvements/differences - TRD Pro wheels, better off-road tires, autodimming dash, auto headlights, better front skid plate, and different grill. You can get the different grill later, but it is $800 or so. Wheels are about a $1,000, tires are about $1200 or so. You can fairly easily make the dash autodim too, there are threads on this. You can also get the skid, but if you have KDSS you'll have to cut the skid plate to fit around the KDSS sway bar. Auto-headlights are doable but look like a pain.
I think that's about it