Re: Upgrade or trade in?
You are looking at a significant amount of cash here. It does help that you the a good starting point for the upgrades path.
The real factor to consider is how attached are you to the pistol?
Right now I have two 1911s that I am facing the same decision on, here is what I plan.
The Kimber Custom II full size. I really like the pistol and have no plans to trade it in. However I am going to be slowly upgrading it. But the upgrades are minor and will come to less than $200.
My carry piece, which I like very much, is an older Kimber Custom Compact. To do the upgrades I want to it would be over $500. I can trade it in and get a new Pistol for less and still get all the upgrades I would do to it anyway. In this case, the trade in makes sense.
In your case, I see a boat load of upgrades to the current pistol. If you really like the pistol (or have an attachment to it)and plan to keep it for years, do the upgrades. If it were me, I would save up and trade it in.
When asked why I wanted my CCW, I was tempted to say "Fishing".