Mine leaks all over as well but not enough to bug me since I don't drive it daily anymore...
There are a bunch of spot welds on the window mount seam, they can rust out, as well as the 4 sheet metal seams in the corners. Other than that depending if you have a solid or sliding window the seal changes some. It's been a long time since I've had a solid window but I don't think it has any drains or anything, just a seal around the whole thing. The sliding windows have drains in the bottom corners or near the bottom corners of the opening, if these are plugged water can get through the seal between the sliders.
The window is really not all that hard to get out and in with one person and maybe a helper... assuming regular cab. To get the window out open a door and push out on a top corner of the window until the seal folds over the sheet metal seam in the corner, now keep pushing along the long side until the top is loose. After that pull the top out until the window is free... Reinstall can be done several ways, I usually do it with a butter knife or spoon or something simple, start in one bottom corner and get the bottom done first then work up one side at a time, just don't go fast and cut the seal. I remember it being much easier to do the Ranger window than it was to do the one on my F350, that thing is huge and the interior trim gets in the way where my Ranger has none... If you take the window and seal out, check for rust and rough spots, seal them up with silicone or at least some good protective paint after proper cleaning.