I am not certain what you mean when you say "you want the male to be a little experienced for next year"?
In my very limited experience with breeding snakes, it has "appeared" much easier for an experienced breeder male to get the job done. I would like to breed the male to five females next year, and I dont want to miss windows of oppurtunity waiting for him to figure it out.
Also the mention of sparing an extra shed to avoid risking slugs? I think you need to clear your mind and start over. For older snakes it is easy to see them fall into a predictable routine for cycling and breeding however some will go like clockwork and others will be a little different as far timing from year to year.
Understood. 
I do not feel there is too much of a predictable window as far the timing of everything involved in reproduction. Even when you say the female seems willing....do you mean she is flagging and gaping her cloaca...or twitching her tail around? Sometimes tail "whipping" seems like an invite to attract the male but it can also mean get the hell away from me too.
She made the male play catch-me-if-you-can for about three minutes. Then she stopped and lifted her tail while he moved up and down her body. After about ten minutes of that she slid to one end and stayed there till I seperated them.
All in all, if I understand you correctly my advice would be to use the male with the best chances of successful reproduction and let the "inexperienced" male wait another year if he is small. If you have that male for a very specific project and are worried it may not come to be then maybe you should reconsider breeding the female this year as well.
Well she could make some decent genotypes with him, but she is part of my ghost project and will be bred into it this year. . .after one more try with the other male.
I hate a quitter 
It is my opinion that male snakes can be lousy, awkward and downright stupid breeders no matter what their age or how many times they bred in the past. While others are champs that grab thier mate, get the job done fast and efficiently and do so time and time again. If you feel I am off base or missed something just post again and I will try and better explain myself Tom Stevens
Thanks for posting Tom,
Ian Daviss