Why didn’t Gandalf better prepare Frodo?

Going over the timeline I see there were about two months between the time Gandalf told Frodo about the Ring and when he left the Shire for the news in the south. We know that Gandalf was not immediately concerned for Frodo’s life, and as yet had no idea that the Nine were approaching, but he was generally worried about the secrecy of the Ring and Frodo’s movements, and thought the journey to Rivendell treacherous enough that he would probably need to escort Frodo there. Even if Gandalf had no reason to believe that he would not accompany Frodo, surely he might have anticipated that they might be separated at some point along the way. So why didn’t Gandalf do more to prepare Frodo (and perhaps Sam) for the upcoming adventure? Of course there wasn’t enough time for a full Ranger training program but they could have studied maps of the road, reviewed safe lodgings along the way, discussed trustworthy contacts etc. Instead we see that Frodo has little or no knowledge beyond common hobbit lore and the facts of Bilbo’s story. He doesn’t know the true dangers of the Old Forest or the Barrow Downs, or of the presence of Tom Bombadil. He doesn’t know about Aragorn, or how to contact any of the Rangers. He doesn’t know that Weathertop is a key landmark and possible rallying point along the road. He doesn’t know to look for hidden runes that Gandalf and the Rangers use. He doesn’t even know about medicinal herbs like athelas.

Obviously from a storytelling perspective it’s more interesting if Frodo doesn’t know this stuff and has to learn it, along with the reader, through his adventuring. But still, it seems like Tolkien could have given us some explanation for why Gandalf never bothered to clue him into some fairly basic and potentially very useful info.
 
As far as the route and lodging, the route is simply the road, and safe lodging would be whatever inns lie along it. As for contacts, Gandalf did try to tell Frodo about Aragorn in the letter that Butterbur never sent, and I can't recall if Gandalf knew the hobbits would trek through the Old Forest, and that a meeting with Tom was at all likely.

I'm guessing it also simply didn't occur to Gandalf that he might need to leave hidden runes, seeing as how it's rather unlikely that he would be close enough to Frodo for Frodo to find the runes, yet unable to actually meet up.

Athelas is an interesting point, but keep in mind that its properties are primarily spiritual in nature. It may be able to help small wounds, but its primary purpose is to fight evils such as the Black Breath or Morgul blades, and what are the odds Frodo's going to face anything like that along the road? After all, Gandalf doesn't yet realize that the Nine are abroad, or else he would have taken Frodo away immediately.
 
In a similar way that Sauron's weakness is never imagining that they would try to destroy the Ring, even when it seems like an obvious possibility, it looks like Gandalf's weakness is never imagining that he won't be present for these critical events like Frodo leaving the Shire, or actually getting in to Mordor, or whatever. Even when it seems like an obvious possibility.
 
In a similar way that Sauron's weakness is never imagining that they would try to destroy the Ring, even when it seems like an obvious possibility, it looks like Gandalf's weakness is never imagining that he won't be present for these critical events like Frodo leaving the Shire, or actually getting in to Mordor, or whatever.
I would imagine that in the same way Gildor describes, Gandalf figures that vague warnings about dark stuff won't help Frodo if he isn't there to explain what's going on, they'll just scare him, so he's not going to give him a partial briefing.

So if Gandalf is there to give a full explanation he can answer any consequent explanations. If he's not there, Frodo's no worse off knowing nothing as opposed to knowing just enough to spook him into doing something stupid.

Even when it seems like an obvious possibility.
I'm not seeing what was so obvious about Saruman turning on Gandalf: I thought we agreed that Gandalf still trusted Saruman implicitly, the Istari essay notwithstanding (and even then, IMHO Olórin just thinks Curumo's being a bit of a jerk, just like he was back in Valinor…).
 
I'm not saying that this specific cause for Gandalf's absence was obvious, just that it seem obvious that there could be "some" cause for his absence, either permanent or temporary.
 
Not sure how how anyone would prepare a hobbit for this kind of trip. It's sort of an apprenticeship learn-by-doing kind of thing. Frodo was actually the most prepared of any of the hobbits already. What more would you teach him? His worldview shift was amazing enough (satisfied hobbit going into exile)... to put him through a boot camp isn't plausible.

And it was unimaginable that Gandalf would disappear, anyway, making additional training unnecessary. Only 2 known powers could have managed that.

And later, Gandalf admits that maybe it was the best thing that Frodo went without him. Most of his advice should have been obvious, and likely ignored (i.e., Don't get drunk and sing on tables in a common room. Stay away from barrows.)

And knowing Gandalf, he'd have ridden on to get a look ahead, only to return to find them in a baffling situation when he came to look behind. "The cow jumped over the moon? Fool of a Baggins!"
 
I think, a possible thing Gandalf might have done is convince Frodo to take a mini-holiday out to Bree some time in his 30s or 40s after the Party. Get him at least a little bit ready for the outside world. You could argue that even if he didn't know everything about everything yet, it would be a good precaution.

It might also have been worthwhile to introduce him to Aragorn. This came up for me many times during the Bree chapter, and was never really resolved to my satisfaction - if Bilbo and Aragorn are such great friends (and it seems like it truly is a wonderful friendship - it's never made explicit by Tolkien to my knowledge, but doing SilmFilm led to me/us really examining the possibilities of There-and-Back-Again Bilbo encountering 10 year old Estel in Rivendell twice, and how they would naturally connect as kindred spirit Mortals in Faerie, becoming boon companions and life-long friends), why does it literally never come up until Rivendell (other than one cryptic and easy to miss spot where Aragorn didn't realize Bilbo had translated the Gil-galad epic, implying that he knew something of Bilbo)? I can think of one reason not to do so - for Ring-management purposes it might have been best to keep Bilbo and Frodo isolated from each other. But that's the only thing I can think of. Otherwise, there are plenty of reasons for Aragorn and Frodo to have been on the best of terms throughout the period between the Party and Frodo's departure, whenever Aragorn wasn't off on some other adventure.
 
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