Has the booster been tested? Engine off pump the pedal until hard; keep pressure on pedal and start engine; the pedal should go to the floor if the booster is good.
How many clicks to set the parking brake? Should be 3-4 clicks. More means the rears need adjusting.

 

I will check on the booster and parking brake clicks tomorrow as i just finished up as it started raining. I bled the master cylinder and gravity bled the lines. I'm 90% sure I didn't let any air in but I'm no professional so it's possible.

I'm not thinking it's a bad booster/vaccume leak as I think that would cause a stiffer pedal but im also not super experienced with all this. Can someone explain how a bad brake booster would cause a soft pedal with more travel?

 

Bad booster, less resistance to pedal pressure allowing pedal to go to floor.

 

Booster Test
With the car off, I pumped the brakes until they were hard. I still had about 2-4 inches of play with the car off. Started it up with the foot on the pedal and it went close to the floor but I had to push it to get it on the floor.

Parking Brake Test
I live on a hill so I turned the car on and put it in neutral. 3 clicks it still rolled. 4 click felt like there was some contact but not enough to stop the car at that steep of a grade. 5 clicks stopped the car.

After this I'm thinking it will be a brake booster. Considering that the OEM one lasted 170k miles and the first replacement was defective, I think there's a non-zero chance that fluid leaked into the booster. Currently I am not losing any fluid. Is there a way I can check to see if the booster has fluid in it without removing the master cylinder or booster? I noticed there is what looks to be a plug to the left of the mast cylinder on the booster, is it safe to remove that for inspection and replace it with added rtv?

 

5 clicks is way to much , 3 clicks is perfect, I adjust mine every oil change.
what you explain about the booster test indicates a failed booster

 

damn alright I'll get that booster ordered. Is a booster a part that can be replaced by an amateur? I'll look into how to adjust the rear brakes as well.

 

I would adjust the rear brakes first. There are lots of youtubes on the subject. 2006-2008 are different from 2009-2011.

 

Will do, and if the rear brakes don't hold an adjustment then I assume I would need to replace the adjuster screw?

 

I thought you said a mechanic did the job and replaced all hardware. I hope that means the universal spring and all of the adjusting bits in the correct orientation.
I don't know what "hold adjustment" could possibly mean. They are either adjusted or not adjusted. It sounds like whoever did the brakes was learning how on your car.
While doing the adjusting you HAVE TO periodically step on the brake pedal to center the pads.

 

Don’t step on the brake pedal if you removed the drum to access the adjuster star