The item handle crash is probably the biggest concern of mine. I assumed that deleting the gold items would free-up the used item handle, if that isn't the case then this system could potentially create that crash quite quickly. Also, if that's the case, then every game is doomed to find this crash eventually regardless of any clean-up done by modders...
The handle might be freed but it is never usable again. The reason for that is the way the handle generator works.
All you can do is change things in a way that not too many handles get created. I changed my Field Bed skills for example to achieve this. Originally it was done with SpawnItem(), but when I learned about the handle thing, I changed that. Also, the TreasureTable cleanup was done because of handles. (e.g. I removed all lockpicks and disarm kits from traders because I introduced the 'unbreakable' versions. One wasted handle less is one less.)
What you can not control is if players craft a lot or split stacks a lot, so it's always a good idea to do as few creations in a mod as really necessary to minimize handle waste from the mod's side.
(You also cannot control how often players learn the spell even if short of money.)
Books in existing games would still get a "free" use, yes, but they've already either paid for the book initially or found it as a drop, so it's not actually free. I really hope no one would complain about balance with this system, it would only be the difference that players do not need to go to each vendor to buy the separate books anymore--if they've already bought/found it once.
For the vendor skillbook stock, I think that, given this system, I would ideally either have books as only drops, or vendors would have a few random books from a pool at a time. Perhaps a mixture of both. Of course, this may be strange to implement in the middle of saved games, etc.
You love to forget crafting ...
From a pool at a time is exactly how it is now, even if the pool might be too big for your taste. This pool is recreated in certain intervals or on levelup, a big pool uses more handles, a small pool less.
I would need to go find pre-placed scripted books, you're right. That shouldn't be too painful though.
It's not, but changing pre-placed items (the objects themselves, not the root templates) once they're initialized has a good chance to render a savegame unusable. Not saying it will, only that there's a chance.
I only want to implement this for running games insofar as I don't want players using the mod to lose their saves. It's possible to do a "re-release" of the mod at some point, with story scripting updates, but I'm not certain about this. I did have an idea for a standalone Epic Encounters release, but this would be something for the future and DoS 2 will be out soon.
I haven't tried raising the max stack size of the good template. Even if I raised it so high that players could never fill a stack, it's possible that players could create separate stacks themselves, causing the system to misread gold (I'm not sure if I would care about this though).
This is an independent problem.
Increasing stack sizes is one of the measures to push the inevitable out-of-handles crash further away.
Anyway, if you want to do it the way you suggested, do it.
The original question was if it could become a problem and I'd say it can, but it depends on player's playstyle. Although you unnecessarily pull the ooh crash closer, it's of course not guaranteed to happen.
And don't forget that you have a complete new area with a lot of objects using handles, the free pool is already reduced compared to standard Enhanced Edition ...