It's commendable you want to fix this yourself but there is no u-tube nor could one be made to cover all possible reasons door isn't closing/fitting right.

Photos showing door type, age, and its issues might help with getting suggested things to try. If you have a level, confirm that it's the door that is askew and not the frame.

Doors need to be plumb, level and square. My bet would be it was installed out of plumb but without more info, impossible to be sure. Post picture's.

Or the door could be slightly warped. Need pictures.

Sorry, I've been trying to find a chance to update this since we have a second little boy running around the house now. I believe that these are Pella, fiberglass doors (3' x 7' x 1.75"). It seems pretty even all the up and down the door. I have to close it maybe 1/8" to get the dead bolt to engage. Could the weather trim be too thick? We have the exact same door in the back with no problems. I would like to put a smart lock on this door, but it will not be functional unless the deadbolt latches freely without having to hold the door shut.

Thanks for any replies and suggestions. If you need me to post anything else, I can try to do that. Here's a video of the door.

I'm glad you posted the pictures,I'm anxiously waiting to see how people diagnosis it and how they say it should be fixed after seeing pictures they requested. . Frankly I don't understand why pictures were requested but now we will see where they lead. Based on my experience with dozens of poorly fitting doors and those I've watched carpenters deal with I couldn't commence explaining the procedure, with or without "pitchers" but I'm ready to learn.

Pics that we can actually enlarge to be able to see the entire door and frame in one shot would be great.

Here are some more pictures.

Any other advice or suggestions?

I cannot tell much from the pictures. It may be an illusion due to the colors but the reveal at the head looks smaller on the hinge stile than the latch stile and the lock rail reveal looks very tight, and the backset dragging on the frame leads me in the same direction. My bet is the door is not hung square and plumb.

It looks like there’s weatherstripping. Is it a bit too thick?

The top weatherstripping looks like it comes out further than the sides. Is it hanging at the top of the door.

The "leaning out" comment is probably why pics were requested. Nothing wrong in commenters trying to get more info in the quest to help someone.

If everything is level, plumb, uniform gaps, and your weatherstripping is uniform and intact, then it is probably the placement of the deadbolt strike plate. You do want the door slab to compress the weatherstripping a bit - especially in your snowy climate, and it is a test-and-set the location of the deadbolt strike based on after the lockset (door handle) strike plate is placed with the door in closed position.

"The door scraping against the frame" I think you might be talking about the latch (curved springy part) hitting the jamb extension (the white painted wide side board). If not and you are talking about the door slab scraping the charcoal painted frame, then something is not square - first check the screws in the hinges are tight.

Is this a new home for you? First winter? Did someone recently install weather stripping or change anything?

We built the home in 2020. It was a custom home. The GCs installed the weather stripping. Everything is original and nothing on this door was changed. We had the issue from day one, but the GCs were very unresponsive and eventually ent out of business. Thankfully, they finished the home! I just want to fix the problem now because I want to eventually install a smart lock which needs a free moving deadbolt. Otherwise, it doesn’t really bother me.

It was hard to see in first set of pictures but after looking at the additional pictures furnished I agree with others. It's either something minor,something major or a combination of something minor plus something major. Either way,here's how to fix it. Use a framing square,a carpenter's level,a hand plane,flat screwdriver,phillips screwdriver,power drill,drill bits,sandpaper,screws,nails,hammer,nail set,flat pry bar,wood shims,caulk,paint,caulk gun,paint brush,utility knife,possibly new weatherstrip,possibly new door and possibly some other tools or supplies. Watch some utubes,take your time, do a good job and ask question along the way if necessary. Above all make sure everything is plumb,square and flush.