So I haven't gone to jail for the entire game, I've completed the main quest line and am just doing all of the other content now and so I decided it was finally time to get my hands dirty raising my pickpocket skill. I've managed to never get caught because i never pickpocketed, always waited for nightfall, and the very few times i got caught picking a lock or taking something off a shelf in a store i would just use F9 to quick reload because I don't want to get my stolen items taken from me and I don't know if it's possible to get them back after they've been taken away and i'm too lazy to let them take me to jail, interrupt my current quest, and find out for myself.

My point is:

When I get caught, at least when I got caught in Riften (i'll check the other holds in a bit) there are two options for bribery to the guard. They both say something along the lines of "I'm with the guild, why don't you look the other way" but one is labeled with 12 gold and the other has a price tag of 350 gold. That seems like a really easy and almost unchallenging choice. 12 gold to just walk away with all my stuff intact.

I did complete the thieves guild questline and returned the skeleton key but I don't know why there would be two options. Anyone else experience this?

Yes, this happened to me. You are right; this was an easy decision: I picked the 350 gold option.

I think one option you just get from having some skill in speechcraft.

Actually one option, the first option says

I'm with the guild, is this enough to clear my bounty? (12 gold)

The second bribe option says

I'm with the guild, how about you look the other way (350 gold)

That is still paraphrased as I had to alt tab just now but wanted to clarify more