Two things - one, you are likely seeing a lot shells. Everything inside is shredded and there is no confidence the shell isn't damaged. Two, what isn't / wasn't concrete is gone. So you might be seeing 30% of the pre-existing structures.
Weaken some - yes. It will still be a major hurricane when it hits Eastern Cuba. Cuba too is in serious trouble. Santiago de Cuba and the southeast/east are steep mountains rising to 6500ft +. 20+ inches of rain and cat 3+ winds will cause extreme damage. There are not worse places for a storm like this to hit. Two of the poorest and most mountainous regions of the Carribean.
Yea, the NHC was very clear that this evening she was moving out of a shear environment and over warm waters with favorable conditions to strengthen. Not unheard of for a storm to ramp up a notch just before landfall. I recall Charley doing that just before landfall. Charley jumped from a messy Cat 2 to a very intense organized cat 4 in like three hours - right next to Florida.