Is there suppose to be somewhat of a gap between these two? It's like this on both sides. If you look on the corner you can see where the timing cover is actually not flush with the engine block.

 

Your pan looks warped to me. IIRC when I did this my engnbldr tcover was fairly flush to the block, not perfect but better than yours. You're going to be using FIPG/RTV silicone gasket anyways, so goober it up and it should seal the irregularities - that's why we use it. I don't see why it wouldn't seal as long as you fill the gap and have done good prep beforehand.

 

Do you have the bolts installed that would pull the pan up ??

If you pried things the pan may be bent slightly

 

I took all the bolts out and put them back in there respective spots unless the po had something wrong. I don't know.

 

Also. I didn't do any hardcore prying. I used a soft wood wedge gently. Guess I'll take it back off and tap it straight. Sucks.

 

Are there different bolt sizes in the front that pull it up or something? I didn't notice any different sizes.

 

All the bolts are the same. Your pan does look bent to me. I would suggest pulling it off and laying it on a solid surface and with a block of wood and hammer try tapping it to get it straight again. I have a tough time with leaks with a perfect pan. I feel your pain on having to pull it back off again. Been there a few times myself.