Problems with rolling down window...

If those forward glass guides are worn out the window should rock in and out of that track. Does it like up with the quarter glass? If the top giude gives up the 2 stainless glass trims will hit.
YearOne sells a repop of forward glass guide package. A ebay seller (FredrickDodge ?) had the OEM pieces but they weren't cheap.
I tend to think the problem may in your hand though, meaning the regulater.
That bearing assembly at the winder handle may be all you need to replace to fix the current problem. May as well replace those guides and forget it for another 40 years. LOL