Paul,
First congratulations on your Moderator status. Well deserved and I hope this forum really takes off.
Now as far as deciding when a custom rifle's time has come... well, for me, it happens in a variety of different ways.
Probably most often is that you just aren't satisfied with what any of the manufacturer's are producing right now or you want to take something good and make it better or "perfect" for you. Maybe they just don't fit you right, or you wish you had iron sights on a model that doesn't have irons. Maybe it's not offered in the caliber you want. Maybe you just want something different. I've "customized" some of mine and am working on my second "true" custom rifle. The first was niche I felt needed to be filled. Nothing on the market had the attributes I felt necessary for this specialized task. That or I just plain didn't like the ones that did.
This second one is an effort to make a Ruger No.1 exactly what I think it should be. Most of it is cosmetic, since the rifle shoots amazingly well to begin with, but am changing a few of the handling properties to make it more efficient and effective for me. Other things being done to it are case-coloring the action, replacing the existing hollow quarter rib rear sight with a solid one, upgrading the stock, adding a skeleton pistol grip cap, nice inletted sling swivel studs, and an improved forend cap (for the mannlicher forearm). The stock will cut to fit me, not to shadow the original. I have no problem with the trigger, safety or barrel, so they will stay. The factory trigger breaks clean and crisp about 4 lbs. The rifle is as accurate as I need and groups very well. The action will require some tightening but overall is a fine factory rifle.
My hope for the next project is another single shot rifle project, based either on a Farquharson, Hagn or Martini. The rifle will, in all likelihood, start with just the action. Hoping to chamber for some old obsolete cartridge that performs as well as today's "new and improved" offerings. I'm thinking of a Krieger or Lilja barrel, custom sights and other metal work, with a custom stock. Not fancy engraving or exhibition grade walnut, but something nice and made to fit me. I suppose another Ruger No.1 could be made to do what this project will accomplish (as indeed other brands and models could too), but I really have a fancy for those three action types. It's an itch that really needs scratching.