OK the good news is that VW2008 seems to work in Lion. I have only started it up. I drew a few squares and saved a file.
Usually if something is wrong it shows up pretty quickly, like the screen video inversion for Jag under VW 2007 or a bit earlier which BTW fixed itself in Snow Leopard.
The bad news is that apparently my old installer disk doesn't even install correctly even in Snow Leopard. I did my original install back at Leopard and then added 3 service packs to get to my current version I upgraded to Snow Leopard some where in that time frame, so I'm not sure where the installer broke (well if it actually is broken. May just be incredibly slow)
So you ask how did I install it on my laptop? Well I took a chance that absolutely everything needed was in the /Applications/Vectoworks 2008 folder.
I used tar to make an archive of this from my main Imac. Moved it over to my laptop and untarred it in the /Applications folder on the hard disk with Lion installed. When I tried it the installation was complete. A regular finder copy BTW didn't seem to work. YMMV
So I'm good to go on that front. I am just about resolved in spending the $200 for the Photoshop upgrade. Still need to make sure that there are no other programs that I need that will cost a lot to replace before I commit my main Imac to Lion.
You ask why do I bother with Lion? Well even though jumping to Lion isn't all that compelling if the next release is really compelling that would be two major jumps and that can be really painful.
Hope that helps. Key is that you must do your installs for VW before going to Lion and maybe earlier. I just got tired of waiting for Vise to search my disks on the laptop when I tried to install off of my Master disk. Maybe it would have eventually finished but I let it run half an hour and it was still searching under Snow Leopard.
Good Luck!!
--Bryan