Need help diagnosing MISFIRE/rich condition

I know little about fixing cars but I'm not shy of learning a thing or two. My work car has been reliable up until this point. It's a 2004 chevy classic about 235,000 miles. 2.2l ecotec l61

Couple months leading up to this point I noticed a sort of "puffing" or soft "popping" sound coming from the tailpipe intermittently. Not a bang or anything. I also noticed one day looking on the ground that there seemed to be some black material that looks like it may have been blown out of the pipe a few feet from it (my first instinct was soot). But it still drove okay. Today I get in the car and I have a VERY noticable misfire along with accompanying blinking CEL. There is a consistent rhythmic "putting" sound coming from the exhaust at idle and while revving. The car shakes(puts along) and even moreso accelerating from a stop. I don't own a code reader so I borrowed one from autozone.

P0172 System Too Rich (Bank 1)
P0302 Cylinder 2 Misfire Detected
P0442 Evaporative Emission System Leak Detected (small leak)
P0302 Cylinder 2 Misfire Detected

My initial assumption was that the misfire was a result of the rich condition but I'm not sure.
Today I went and got hold of a fuel pressure tester and here's what I got.

KOEO prime: 54 psi
15 minutes later: 51 psi
turning on the car it idles at 60 psi
revving the engine it stays at 60 psi

I removed the vacuum line from what I assumed was the regulator and noticed no fuel coming out of it. (round thing on end of rail) I also noticed there doesn't seem to be any vacuum coming from the hose that lead back to the plenum. I didn't verify this with a tool, I just used my finger to feel for it. I don't know why there would be a vacuum hose where no vacuum was but that's why I'm here asking someone who knows more than me lol.
I'm just spit balling, I need direction. Where do I go from here? Is it reasonable to start looking at ignition system components or have I not correctly/sufficiently/reasonably assessed the fuel system? (at least that of which is reachable under the hood)

EDIT: I just used one of those hand vac pumps to manually pull a vacuum on the nipple at the regulator. I was thinking that maybe if the diaphragm was stuck closed for whatever reason, I could manually lift it with the pump. The fuel pressure did drop by using the pump but it seemed to make absolutely no difference on the misfire.

Are you getting spark at number 2 cylinder?

It has a large coil assembly like this, how do I go about checking for spark at cylinder 2 with this type?

I replaced the plug in the suspect cylinder with a new one and it made absolutely no difference. I've attached pictures of the old plug that came out of cylinder 2.

Remove the coil use spark tester check for spark while cranking

I keep a set of old plug wires around so I can check each tower with the car running, but Cheryl is right. You can have some one crank the engine while you check spark with the out of the engine.

I went and bought a spark tester light earlier along with a compression tester.

Just so I'm understanding it would be a safe and valid test for me to disconnect the coil pack assembly from all plugs and insert the tester between the coil and plug one cylinder at a time while the engine is running? Could I also look for spark with a screwdriver at the end of the coil or can that damage anything?

Could a vac leak cause no vac at the regulator?

I found this hole in my intake manifold, I'm not sure if it's just made that way or it's an actual hole. This is below and in between injectors 1 and 2.

I laid the coil pack on it's side with the 4 outputs about a quarter inch from the grounded valve cover. Cranked the engine and #2 did in fact NOT have any spark at all while the other three did. I haven't put the replacement in yet but I really hope this fixes the misfire, I'm sure it will. Thanks guys! As for the rich condition, I'll look into that shortly after I get this new coil put in. Like was mentioned here could be two seperate issues.

That hole in the intake manifold looks too clean but I checked ebay images and it's normal. Phew. imgur.com/a/g1XsYxi