Sorry I ben off here for a "LONG" time. Finally got an updated computer and a project. Wondering if I'm in the right area, looking for paint and body input, more so body. Have a 68 F100 that needs some general 50+ year old attention. Love to pick the mind of those in the know on how they would approach these repairs. If the images load the cab has a roof bruise that is not dolly friends and the rear corner must have caught a stump. Already drilled out the spot welds on that area with a I dunno wtf idea in mind.
The dent comes out the exact opposite of how it went in. Meaning, the crease in the center is the last thing I'd touch. Work form the outside in. Heat, just enough to loosen the electrons and make it malleable, dolly off hammer around the crater rim. Push the metal back into the cavity. A few studs welded in the perimeter will help pull the lows. When I am the luckiest at dent extraction, I never touch the extreme center of the dent. The metal could have stretched (most likely) so some shrinking may be in order. Personally, this is one of my favorite type dents. Easy access to the rear, non structural, nice metal, thick Henry Ford steel...have fun with it. It is hard to F up.
Right now is probably the best time to get tips from metal guys, in that you can select from dozens of people that have video tutorials on stuff like this from the comfort of your own home. It will come down to actually doing the work, but seeing how a bunch of pros do it with stop, rewind and repeat it is just shy of having them lean over your shoulder and talk you through it. I like this guy's sense of humor and skills with basic tools, but you should be able to find one who works for your own learning curve. https://www.youtube.com/@CarterAutoRestyling/videos He straightened the roof before chopping a year ago, which should get you started.
Buy a copy of this. https://www.amazon.com/Martin-BFB-Bumping-Manual-Instruction/dp/B001GUZP4O It will reinforce what Billy said in great detail
I had a dent in the cab of a similar-era Chevy truck almost identical to that one, we welded a plate in the center of the dent with a hole in the plate, hooked a come-along to the plate and cranked it up against a beam in my buddy's garage. Not enough to pull it all the way out, but to get a good amount of grunt pulling up. Then you can start hammering around the dent and kind of "relax" it out, tightening the come along a bit as the metal starts to move to take up whatever slack it gave. A bit of heat probably would have helped too, we got a bit brutal with it in the end and should have had a little more patience because it was working. I ended up getting it "close enough" and filled the rest but with patience and persistence I think you could get that very, very close.
Before I'd give advice, I would want to see the other side. I see a horizontal rust line above the panel seam. That warns me there's an inside panel that probably has something to do with the window opening. You also said 68 F-100. that tells me there should be a full metal inner headliner panel. If so that brings a totally different approach to the job.