So i've recently begun trying to become more accurate pitching/flipping and have even attempted skipping. (Failing horribly @ skipping)

I've begun to notice that my baits really dont fall straight down. In fact they tend to hit the water and sink a little and then pendulum back towards me. I think this has something to do with my spool tension being too tight? I usually set up my bait cast reels by setting the centrifugal brakes, then adjusting the spool tension so it hits the ground with no over run.

Should I just loosen it and feather more during casting? Or is there a simple fix I'm totally over looking?

either pull some line out by hand or drop your rod tip so the bait will fall on slack line.

Falling toward you is normal, just pull out some line so the bait falls on slack line. Read somewhere that this is why pitching with spinning gear is easier just leave the bail open, with baitcasting equipment you have to physically pull out enough line.

Say I'm pitching to a specific spot, a stump. Wouldnt it be more advantageous to have it drop straight down near the stump than start to pendulum back?

Yes, that's why you manually pull out line. Watch a proficient cover fisherman. They pitch it in and pull line off the reel. There is really no other way to do it. Pulling line of the reel will allow the bait to drop vertically. If I'm pitching deep cover I'll switch to a spinning reel and just leave the bail open. Nothing more aggregating than a hard run with an open clutch on baitcasting equipment. More than once I've set the hook and create the ultimate backlash

You've got several options. One, in clearer water,the bait swinging kind of away from the cover isn't necessarily a bad thing. It creates the illusion of something trying to escape from whatever object you'[ve thrown at. Two, sometimes you can throw past the object so that it swings into your target area. Thirdly, feeding the bait line isn't that hard to do. You don't even have to use your off hand to pull out line. Most of the time , when I want a more direct fall, I'll just kick the spool of my reel with my thumb, release some line, and then just stop the spool with my thumb again. I'm not saying that I never backlash my reels doing this, but with practice you backlash less often than you might think.

Option 4 is to pitch the target using spinning gear, which also isn't a terrible idea.

Cool thanks everyone!

Psyched myself out thinking it must be a bigger problem than it is.

this is why you see some guys end their pitch with the rod tip held up high...that way, they can just drop the tip to allow the bait to fall straight.

If you finish your pitch properly, your rod will be at 12:00 and the reel engaged. That should give you plenty of slack to feed the bait by dropping your rod tip as the bait falls. This way, you'll be in better contact with the line to feel a strike on the fall, rather than clumsily setting the hook while peeling line off the reel.

Anyone think of any videos that demonstrate this? Most just show people doing it so fast I miss those kinds of details.

The lunkerville episodes with Ronnie Jighead show it real well.