Welcome to the site!
I am buying my first CVO bike this week. This will be my 4th Harley and throw a Victory and Kawi in there as well. Just could never justify the extra expense of the CVO. Problem is, mentally, I tried to turn each one into a CVO - meaning I spent a chitload of $$ on them. I submit that if I had just spent the $$ upfront and gotten the CVO, I'd be much better off financially. I hang out quite a bit at a local chop shop that specializes in upgrading stock bikes. Most guys that bring their stock baggers in there spend $8-12k fixing them up. Wheels, chrome, motor improvements, paint, etc. So if you spend $20k on a stock and add the eventual "trickle" of $10k, you are not far off from the $33-34k for the new one (with engine mods). That's my justification.
Hope this helps, and YOU ROCK dude. Our guys in the armed forces are the KEY to the success of democracy and our way of life. Without your sacrifice, none of us would even have this kind of decision to make.
Brad