In your example you are dealing with a limited gene pool so with all the inbred crossing and back crossing what you are really doing is exploring the contents of your plants genome. After four generations (probably hundreds of seedlings) you will have a pretry good idea of whats in there.
What most breeders do is just self the plant. Its a simple way to make a living punnet square of possibilities based on the plants genome, and its the same hybrid (your strategy makes plants which all have different hybrid names) if there is potential for something amazing in there, you can get it out by blooming dozens or hundreds of progeny. It really isnt roulette at all. You just need to be able to grow out tons of plants. No way to know for each one, but as a group they are predictable.
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