First, welcome to the forum.
Second IMO that speaker begs to be stolen, but until that happens it looks alright. (Maybe I just have bad luck, but anytime I put anything 1/2 visible it grows legs...so I've stopped doing that.).
Look at your rear diff. cover from the back... If it has a metal fill plug consider yourself lucky as you have a Dana 44. If it has a rubber fill plug its a Dana 35. which isn't a "end of the world" type of thing, but its not the best you could hope for either.
On gearing, do it once. so if you plan on getting larger tires in the future, I'd just stick with the OEM gears until you up it...but I'm not a fan of doing things twice. (its expensive, and I'm cheap).
many say DD on 33's is fine with OEM gears, but I don't know which gearing you have, and I'm not you, so that's one you'll have to decide on.
I applaud your enthusiasm, but damn those are some dark pics