I would think that the more you do the better you get, since you will build a collection of jigs and tooling to overcome all those hurdles that everyone runs into when they do something for the first time, plus you will have an ever increasing level of experience.
The more you do, the more of a production-line mentality you obtain to increase you work-rate and your success-rate.
Whenever you do a model engine for the first time you are in a similar position to the professionals who built items like Concorde or the Apollo programme.
The first effort is always a prototype, a bespoke effort which exists on paper but you have to create a working reality of the paper theory.
Concorde is a great example.
It over-ran by huge amounts of money, I recall one politician saying that they simply stopped counting how much was being chucked at it to get the first one into the air.
So the professionals often have the same problems on a bigger scale, how much government stuff has overrun by millions and been YEARS behind schedule?
This guy makes one eentsy weentsy diesel engine, check out the setup he has just to achieve a reasonable production rate with a decent accuracy.
http://modelenginenews.org/pb/index.html