Couple thoughts:
I think general practice is that your rope should be your weakest link in your rigging system.
Remember that published WLL is when your rope is new.
I agree with the idea of "crash landing" your logs into the dirt as you get lower on the trunk, with a rigging line to control the fall, and stop the butt from crashing down onto your obstacles, rather than arresting the fall.
Focus on efficiency, not necessarily rigging the biggest pieces you can, especially when working in the tight space you have. Sometimes, safe and big is best, other times, not.
Butt wood might be heavier than higher up. Slower growing trees might weigh more than faster growing trees. Wet side of the mountains might weigh more per cubic foot than the dry side of the mountains. Dunno. Suspect so. Remember that your working off an averaged green log weight chart. Without a scale, you don't really know what you're rigging.
Sounds like if your break a rope, you could have significant consequences (aside from getting whipped by the rope).
You can put a block at the base of the removal tree, and mount your lowering device on another tree's base in order to introduce greater lengths of rope into the system as your get lower. With the GRCS, I reckon that you'll be needing 3 full strength blocks instead of one, as you'll need to fairlead into the top.
If you'll be bucking logs, getting them out of the dropzone quickly may speed up the process, so be prepared for that, as applicable. I spin logs manually by rolling them onto a branch (perpendicular to the log) as near to the balance point as I can, then spinning. I've spun some decent sized logs this way in order to winch them in top or butt first to load them on with a knuckeboom, and to roll them out whole to the front yard. This 'pivot' works well to keep tapered logs rolling the right general direction when they want to turn due to the taper. In this tight drop zone, you might have to buck a log in half or thirds to have groundies roll it out if by hand. Perhaps you will winch them out quickly, or have a machine to pull them out one way or another.
If you decided to crane the trunk wood, after stripping limbs/ top, and the trunk is basically vertical, it is about as easy of craning as it will get. That's not to say it will be stress free, but you could consider it a building block if you're newer to crane work, but have the necessary skill, have a good operator, and it might be more beneficial to the HO and/ or crew. If not, hopefully you and your ropeman are a good team.
How 'bout them pics??