I keep my mix almost completely dry, for what it's worth.  If the cup has so much water in it that it feels "heavy" or even has any significant weight to it, then you're probably overwatering, and can/will suffocate or kill the roots.  Condensation on the side of the cup is normal, but if you can see your potting material stuck to the side of the cup completely wet, you're probably overwatering. 

I've gotten to the point where I'm using a much chunkier, looser mixture (lots of Perlite, no vermiculite, with a little half-scoop of non-soil, non-slow-release-fertilizer potting mix), which leaves me watering every 3-4 days, but the water - for the most part - runs right through the mix.

I attached two pictures to try to demonstrate what I think is "proper watering". 

The clear cup, this is just before I watered.  There is no condensation on the sides of the cup.  The material is not "clearly wet", and it is not sticking to the inside of the cup.  The lack of condensation, and lightness of the cup (it feels almost empty) is my indicator that the potting material is not wet enough.

The orange cup, you will notice that there is condensation, but no actual "clearly wet" material inside the cup.  None of the material is sticking to the inside of the cup.  The roots are happy.  This cup was watered the night prior to taking this photo.

I went through that experience. Leaves suddenly "droop" and eventually
the whole (rooted) twig dies off! On a close examination (in my case), I
had noticed that the twig rotted somewhere between the roots and the
leaves, thereby "breaking" the pluming connection. I did manage to salvage
a very FEW by "upping" the soil, together with a (vented) dome.
Others do cut off the (bottom) part of the rotting twig and re-plant the
still-good top-part. In both cases, one hopes that there is still enough
energy left in the wood? (which sadly, most often, usually is not the case).

In my past post-analysis, when rub/squeeze-ing the mid section -
the dark mushy bark  just came off.

Have you had mold spores apear in top of the soil mediums?  I did, and this was right before all of this started happening

yeah mine had little white balls of fuzz all on top of the soil

Gorgi I lost atleast 10 cuttings this year this way, I made sure I prewet the medium first and used allot of perlite in the mix and was usually 3-4 when I checked with the moisture meter. However I did have all the ones that died domed for about 3 weeks unless the condensation from the cups made the mix too wet or it the moisture in the cup was way too high not sure.

Thanks Paul will keep my fingers crossed. Its True Martin, Paul really is a great genuine guy and has helped me out allot and im very thankfull for that.