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I have an orange 2x12, I'm replacing the speakers with a single 12 inch speaker for now (will add another later)
That said:
1. Which tab on the speaker do I hook the speaker wire up to?
2. Is it ok if the speaker wire splits into 2 but I only have one speaker hooked up to it?

Think I figured out that one end of the wire (that is attached to the tip of the jack) connects to the positive tab on the speaker and the other (that is attached to the sleeve of the jack) to the negative
How do I figure out which lug is the 'tip' and which is the 'sleeve' on a plastic enclosed jack like this?

The lugs closest to the input are the ground, and the ones toward the butt of the jack are the tip!

Cool! Could someone please let me know if this wiring is correct then?

Yep you should be good to go

I'd run a jumper from one lug to the other for both the negative and the positive as well, so that both lugs connect

As in, the front two lugs connect, and the back to lugs connect. But not the front lugs to the back lugs

Like so? Any advantage to doing that? Didn't come like that from the factory is why I ask.
The lug I choose on the speaker doesn't matter right?

No real advantage honestly. If it didn't come like that then I wouldn't worry about it! I'd just wire the speaker to the lugs that were already soldered to