Alright so made it out to the garage on Saturday and didn't have the best of luck. I realized that taking off the fender meant also taking off the hood, and it just wasn't going to happen that day. I was able to get a rachet and socket on the bottom bolts on the cowl, and was loosening those and trying to get the door up. However, since the door had to be open to loosen/tighten those bolts, it was hard to jack up the door into place. So after a couple times of doing that, there was still no change.
Then decided to add some shims on the bottom hinge (door side) to get it to push the door out some (I know, was told not to because it's not professional), but is only temporary until I find a body guy. Everytime I take the car out to shows, always run into body guys who want to work on her. So that pushed the door some, and then moved the striker up a little. It fits, not perfect, but much better than before still. I'll work on it some more, but just short on time do to personal stuff right now. You can see in the attachment that it fits decent. If you're looking specifically at the alignment then ya you can tell. But again, just needed it in place where I can drive it for the time being.
As far as the drivers side, it looks like I can do the bottom, but the top the pins go into the door if taking it off, so wouldn't work. Also, that little roller that rolls along the track to where the door opens up half or full way, is nearly off the pin, which explains a lot on the drivers door. So I feel I can rebuild the bottom first still entirely on the car, but will have to take off the top entirely. Hopefully, that all works out. No idea when I'll get to that though.
Bought a full set of the T bits from AutoZone. Was $13 for the set, and much better than what Harbor Freight had. I believe it was a T24 for reference.
Again, thanks for all the help.