chaim, I've been there; done that exact thing. Decided I was going back to the drawing board and selling everything if necessary and greatly scaling back, and replacing several lower quality guns with fewer high quality/expensive guns, and get down to just 3 or 4 calibers, not counting shotguns, airguns, and MLs. But the problem is, I just can't stand to part with some of the guns that I don't "need" - ones that don't make sense or fit into my new simplified scheme - a good example is the Marlin 1895 levergun. So the list keeps growing and growing to justify the ones I cannot bear to sell, and I end up only being able to pare off about 4 or 5 guns when it's all said and done. Then I figure it's not worth it to try - if I'm not gonna do it right, I shouldn't do it.
But the best thing to do if you're serious is to finish your scheme, and then sell guns one at a time over a long period of time by placing them for sale at a very healthy price - if they sell, they sell to someone who will appreciate them, or if they don't they don't. But at least you won't feel badly knowing that you got a fair price for each that do sell. Use the sales to fund your new scheme