Post some photos, opening up the hole that the channels go into a little big while still leaving it small enough for the window frame to cover it may make all the difference in the world.
Forgive me for my ignorance I don't know these bodies at all, never worked on one in my life. But if it is your typical fiberglass body around the windows opening on the inside is a bit smaller than it was originally on the steel car. It's only understandable that it would be, the fiberglass is thicker than the metal right off the bat, then the body maker let's a little more fiberglass hang off on the edges and wham you have a tighter hole for the glass and channel to go thru and being it was VERY tight when it was steel, it is REALLY tight now and the glass can't even fit thru.
Like I said, I have not done this particular project, but just looking at it like any other problem of the kind my first question of my self is, "How was it installed at the factory". In 1934 how did they install the door glass in one of these bodies? They stuck it down thru the hole from the inside that's how. So what is different about this Outlaw body that is preventing this? THAT
is what I would be looking at.
Now, being chopped makes a HUGE difference in installing the door glass, and even with a stock steel body some modifying to the whole could even be needed, so with the extra challenges of a "new" fiberglass body I can only imagine. But if the hole can be modified in some way to get that window in, and that modification is covered by the inside window frame, what the hay?
Also, putting the glass in on most of these old cars is a challenge, it is a friggin puzzle that has to be figured out, with the channel, without the channel, with the door latch installed, without it, it can be a crazy bare even with a stone stock car. I assume we are talking one piece windows, sticking them straight down is probably out, most often they need to be stuck into the door face down then after it's in the door rock it down in the back into position sticking the front lower corner and upper rear corner into the channel.
Like I said, I don't know these bodies but just thought I would toss out there some general ideas that may be of help.