Yes, I first fit the tranny and than attached pressure plate bolts through the inspection hole. I did it that way because I didn't have a piloting part (an old input shaft) and also because I did a swap of 15,5 clutch by that same way in my R-model. This way you don't have the friction discs loaded so they're free to allow the input shaft to mate the bearing in the flywheel. All in all I assumed it to me as a hard job, mostly when you finally put pressure plate screws. But could be done. And initially I was adviced this approach on here, on BMT.
That clutch in my 1983 (or 82?) Cruiseliner was 14" clutch indeed. The identification is the flywheel for 14" is a deep dish while for 15,5 it's kind of a plate with 4 pedestals. Also the intermediate plate in 14" setup has multiple scuare cut outs over its OD to be corresponded with piloting pins in the flywheel. And 15,5 has four outer lips over it. Both points could be seen through the inspection hole.
My story turned out I had to pull the tranny once more after the time I made that post. The matter was wrong setting of the pressure plate. And I couldn't correct it in the truck since the throw out bearing didn't have any travel (since was set wrong). So after remove of the tranny I compressed the pressure plate in an arbour press, found out the set screw was not seised (what I was afraid of) and corrected the settings. Than put everything back onto the truck (forgot which way I fitted the clutch since I may be having a 2" input shaft from another tranny since that time it was in my yard). And when in place I ended setting the bearing travel and ajusted the clutchg brake (which I put new).
Of other issues worth mentioning I had that central plate not coming onto the piloting pins in the flywheel when put the parts together at the first time. Found that when the tranny was in place and I drove the pressure plate bolts (through that inspection hole and laying on a ground under the truck. So had to release the bolts and make some wiggling and kicking with a piece of steel stock and a hammer and forgot what else).
The transmission in my truck is T1078 5-speed I belive. Very similar to your 6-speed. So I too expect you also having 14" clutch.
Bad thing I did I didn't describe the way I solved my issue in that original thread. If so I wouldn't need typing all this now. But as it usually happens current affairs take you off a subject.
Vlad