It all became much easier this morning.
Well, here it is.
I have here three buttons.
Each of these buttons may have to pressed several times to achieve convergence of that button.
Thie idea is to press the button, look at the result, and then press the button again if needed. 8)
The buttons must be used in the correct order.
Button one must be run to convergence, then button two must be run to convergence, and then button three must be run to convergence.
If you haven't already done so, download Ken's Test Files.
They can be downloaded from his KRA-10StepsToFileNameBliss-TestCases-v5.0.zip link earlier in this thread.
Button One - Removes ( dot | underscore | multiple space ) characters
@NoDeselect
Rename REGEXP PATTERN="(([^_]*|[^\.]*)(_|\.| ))(.*)(\.)(.*)" TO="\2 \4\5\6"
Button Two - Inserts dot characters between numbers relative to (V | v) characters
@NoDeselect
Rename REGEXP PATTERN="(.*)(V|v)((\.[0-9])*)([^0-9])?([0-9])(.*)" TO="\1\2\3.\6\7"
Button Three - Flanks hyphen characters with a space character on each side if they don't already exist
@NoDeselect
Rename REGEXP PATTERN="(.*)(([^ ])(-)|(-)([^ ]))(.*)" TO="\1\3 \4\5 \6\7"
The entire toolbar can be downloaded at the bottom of this post.
This does all of the original problem except the Titlecase Rename.
Ken got the Titlecase Rename in his solution.
I still think a command line program is the better solution here,
but after working on it several hours yesterday and almost failing,
I just HAD to finish it.
@Ken
Thanks very much for your test files.
They were invaluable ! 
Regards,
Porcupine
Filename Cleanup Regex -- Porcupine Three Button.dop (1.56 KB)