First i'd like to thank you again for your ideas and suggestions, i do appreciate them!
1. I'm checking through the VM Summary screen and by checking the VMDK size in browse datastore (like your suggesting basically)
2. I've tried all the options there, i've even tried converting to Thick, sdelete again and back to Thin, I've tried keeping it the same (it is a thin VMDK) and i've tried specifying thing, neither way seems to make a difference.
3. No change that i notice, if it's a minor change it is really a minor change and i'm not noticing the difference because i'm looking at GBs and nothing really smaller. The original VMDK shrink was something like 200 GBs to 30 or 40 (can't remember the specifics now). But this VMDK that i have now should be going from 120 GB to 19.
4. I'll give that a try ^^
5. This is the second VM that is doing this to me unfortanetly, i was really hoping it was either a VM / VMDK specific problem or a problem that was fixed in an update. But at this point, it doesn't seem to be either.
Using VMware Converter with the previous VMDK it noticed the size change immedietly and showed me the difference in the summary. But just to recap, i still need to try the -K, i wll also try doing a vmkfstools -i -d cold clone (just to try) and i still need to try the defrags you suggested. I should be able to get some downtime with that VM tonight so i'll give those ideas a shot.