Just my 2 cents, but I always have figured that when I can afford it, I have permission from the "boss", and when it makes sense, I get the next plane going. I try and plan about 2 planes ahead in terms of equipment just because it is expensive to have to re-buy stuff if you can avoid it.
I always like to have a second plane in the wings ready for gear installation. That way if somethign bad happens, I am not weeks away from flying again.

Tom