Spider-Man 3

Due to frustration and hardly any assistance on other sites I decided to make a solution to this achievement. While Bonkekook has a good solution for 2/3 of the achievement the third mission is somewhat vague.

This achievement has three random side-missions that must be completed. They will happen in order but when they appear/activate is somewhat random. The key difference between standard side-missions and these special ones are Spider Man will make a remark about the situation and one or two have their own cut-scene. Also all three missions occur in the Apocalypse gang territory.

The first mission, a jailbreak, initiates almost as soon as you enter the Apocalypse area for the first time.

The second mission, a driveby, occurs anytime after the first.

Now the third mission, defend an eye witness, will not occur no matter how much you search the Apocalypse territory. You must first complete the Kingpin Part 2 mission. I am sure of this, I started a new game and swung, ran, waited, and even surfed cars for around 4 hours and not a thing happened. Once I completed the Kingpin 2 mission I returned to the Apocalypse territory specifically the square block around the church in the area and it activated after a few garbage side-missions. A police siren will scream by and Spider Man will say something along the lines of "better check it out." Follow the cop car to the New Age Store, talk to the cop behind the counter, hunt down the witness vehicle, disable the vehicle, defend the witness from thugs, and finally haul him to the store front where your achievement will unlock.

Any questions do not hesitate to ask! Good Luck.