***Update-See step 5 for a better approach to fixing this issue. Steps 1 through 4 describe one method that is really sort of more an unnecessary longcut than a shortcut. Plus it wont work if you dont have an oscillating tool.****
I had a door that couldnt be shut without way to much kicking the bottom of it really hard involved. I had two old windows that simply could not be opened. The force that would have been required to open the old windows would have destroyed them.
Old wooden windows go up and down in a wooden track just a slight bit wider than the window. Over time due to wood swelling, humidity, etc for whatever reason the track becomes too narrow for the window to easily slide up and down.
The same basic idea applies to wooden doors. The door is a big wood rectangle that fits inside the slightly bigger rectangle of the door frame. That only works if your door hangs perfectly exactly as it should. Over time, for whatever reason, heavy wooden doors tend to hang less perfectly as they should than they did before.
Step 1: What You Need
An oscillating tool with a plunge cut blade.
Still the oscillating tool should work I think, but it will probably take a lot longer . I personally used a sawzaw. Otherwise known as a reciprocating saw.
Step 2: What to Do: Windows
Take the plunge cut blade, lay it flat against the wood border of the window pane like in the picture. Wherever the track is too narrow, use the plunge cut blade to widen it. Just keep the blade pushed flat against the wood of the window pane. You'll feel when youve plunge cut far enough. It just works perfectly awesomely to make one plunge cut blade's worth of space between the window pane and the track. Look at the pictures.
Step 3: What to Do: the Door
Youve got to feel where the door is rubbing. For rubbing against the frame on the handle side of the door the procedure is the same as for windows. The main problem is probably going to be that the bottom of the door is rubbing against the floor part of the doorframe, you know, the part that's under it when the door is shut. This is where the sawzaw comes in. Look or feel at the bottom of the door, there should be a slight gap all the way along it when the door is shut. There isn't though. Thats why it's hard to open and close, just like the window. Open the door up to where on the less rubbing side of the bottom of the door there is a small gap where you can get the saw zaw blade into it. then just cut along the bottom of the door, the space where the gap is supposed to be acts as a pilot hoke for the blade to cut. The sawzaw blade is slightly flexible so it doesnt have to line up perfectly parallel to the space where it is cutting along, still, though keep the main part of the sawzaw pushed against the floor. Dont put upwards pressure on the blade or it will try to cut upwards like a jigsaw instead of cutting along where you want it to. Anyways just repeat that process with the door more and more closed until the door shuts nicely. Be careful as youre getting to the edge of the andle side of the bottom of the door so you dont cut into the door frame, just angle the sawblade a bit there. Basically use common sense, start out slow and take little pause to observe what the cutting blade is doing. I am over explaining this part, just dont try to beast through it ion one blind cut while yanking up like youre not supposed to and then wonder why things went horribly wrong. A little craftsmanship goes a long way.
Step 4: You're Done
The door works nicely now. Look at the picture in the previous step and youll see that yes the paint was shaved away along with the bit of wood required. Yea, that's how it is. put some stain on it if you want. Or repaint it. But at that point you may as well have taken the door off the hinges and cut or sanded away at the bottom of the door where it would be less noticable. Or moved the hinges and rehung the door. What a pain though. I dont know. Maybe the window fix makes more sense because it still looks preety much the same when your done. Im not like Super Mr. Fixit so if you have encountered a similar door closing problem in the past and fixed it a different way please comment as to what that way was.
Step 5: The Better Way That Makes More Sense to Fix Stuck Windows
Rather than enlarging the track by sawing it wider with a plunge blade and damaging your window, just pry off the front track trim piece that is too tight and put it back on with a little more clearance. using 1 layer of corrugated carboard as a spacer to get the spacing right. Start with a putty knife to pry it just a bit to where you can fit in a heavier pry tool. If that piece like in my case was fitted very tightly you may have to cut off the bottom couple centimeters to get it out.
Now here's where I goofed. It's possible that the window is painted shut from the outside as well as the inside so check that out first. If it is, have step one be to take off the outer storm window if there is one so you can get out the window sash where it's painted shut on the outside side of it. Get that window freed up of being painted shut on both the inside and the outside. and only then if it still doesnt work go on to taking off the front window track piece and repositioning it out a bit to widen the window track. Take out the old nails that were in that piece and tack it back on using a strip of corrugated cardboard to get a generous yet not too generous space, pulling the cardboard out once that piece is reattatched. That is a way better way to fix it and won't mess up your window. You can use the specialty tool to unstick the pain that is suggested in the comments. I'm sure it works well. I used a flat screwdriver. That worked good too and no ones going to be looking that close if its the outer side of the window.
As far as a better way to fix the stuck door without messing it up, I'm not sure yet.