IF the 30-30AI chamber was cut properly, with the neck within the 30-30AI specs, and the case shoulder is in the right position, the chamber neck isn't too large a diameter and the headspace is held by the case rim, there
should be no problems. You will get a perfectly filled out 30-30AI case as the actual pressure produced by the factory ammo will be less in the slightly larger chamber. After that you should set the sizer die to just touch the new shoulder so you will be headspacing on the shoulder rather than on the rim. Lubing the case(I used to use STP to form many wildcats...messy stuff!!!!) allows the case to expand easier. RCBS case lube worked OK as did light weight oil, especially the synthetic stuff, but now I use Imperial sizing wax also(much easier to use) so you have your choice.
In the case of a 30-30, the case has very thin walls already in the upper third of the length or so, so the brass sticks to the chamber walls much quicker and harder than in other types of cases...using 375 Win brass is a very large step in the right direction.
AND, NOT using factory loaded ammo, but rather doing what Tim did or doing it the same way with 30-30 brass, seating the bullet out into the lands and using a midrange load is the best way to get perfectly formed 30-30AI cases.
As always, getting a nicely filled out and formed case isn't always the actual happening using factory 30-30 ammo, you just have to try a few to see. If you're lucky things will work out right.
I did quite a few AI conversions over the years, but the 30-30 didn't have enough additional pizzazz for me so I never bothered with it, I liked the 30 Leverpower better...
, but if I were to do one today I wouldn't use 30-30 brass. Today I would opt for one of several better cases like the 30-40 Krag or one of the slightly larger rimmed cases like the 38-55 or 38-72 or would use 375 Win Brass and start at the beginning with the sizing and bullet seating...the "correct way". You shouldn't have any problems selling or trading 30-30 factory ammo.
You can also use a bullet puller to pull the bullet out about 0.200", then reseat it so it is stuffed into the lands a bit. This will hold the base back against the bolt face and allow the case to be formed WITHOUT moving backwards.
Luck