about・approximately
Structure
- Number/counter + くらい or ぐらい
Is there a way to predict when くらい gets rendaku? Or is one to learn this in a case-by-case basis?
I mean, as far as I know rendaku is impossible to predict, but I figured it might be worth asking on the forums
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Those two can be freely swapped without changing meaning 
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But isn’t it the case that one sounds more natural after a given word, even if they mean the same thing?
ぐらい is used more often since it easier to pronounce for most people. But if you find くらい easier to use then use it instead. Basically, everything depends which is easier for you to say.
Originally くらい was exclusively used after demonstratives (この、その etc…).
only ぐらい was used after nouns and pronouns.
And both could be used interchangeably for verbs, (い、な)adjectives and auxiliary verbs.
But it is no longer a rule.
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For this sentence:
14歳 ぐらい から、私は仕事をした。
Is there any reason ほど shouldn’t be accepted or at least flagged for warning? I’m still finding it hard to decide which to use because there’s really no way to differentiate in the English.
In the example sentence…
100万円ぐらいかかります。
It costs about one million yen.
How does かかる translate into costing an amount? I looked this word up and got bombarded with as many as 14, wildly different meanings. This hurts my brain >_<. Any insight into this word, would be amazingly helpful! 
It’s the first definition on jisho. 
to take (a resource, e.g. time or money)
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I recall talking to my language partner about this and I asked if they find the all the definitions confusing but she didn’t.
So I tried to break it down into a marco definition so the subheadings would fit in my brain: “to begin a connection and keep that connection” is the closest I can get that works for me. Then I separated out the sub-groups:
More physical direct object-y (no to be confused with かける）
-to hang
-to cover
-to fasten
-to start an engine
-to connect a phone call
-to put on glasses (sorry, this is かける）
Action
-to take resources
-to come at
-to deal with
-to be caught in
-to overlap
Time
-to take time/resources
-to arrive
-to attend
-to depend on
-to come under contract
Using it in my own sentences is another feat that I’ve yet to master but having a discussion like this is very helpful start (sorry for the derailing on the くらい thread 
everyone). Certainly open to suggestions on how to digest this beast.
Edit: Need a separate entry just for the non 掛 word plus the additional +30 かけるs!!!
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Thank you, thank you, Seanblue and you too, s1212z for fantastic answer!
Its nice to see you two again, haha! Though I know its sure going to take a lot
of reading to make かかる and かける feel natural, but at least now I have a
picture in my head, Thank you!
Also yes, apologies for derailing くらい thread!
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This is a minor, visual thing, but 「くらい ①」is preferable to 「くらい①」to me.
eta: Interesting… when I posted this the space between くらい and ① was removed, or at least, reduced. 
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それぐらいでいいです。
Was wondering why the で is needed here after ぐらい?
Without the で, the …ぐらい works like an adverbial phrase that modifies いい: “It’s about that good”.
I’m a little confused as to why for the following english sentence, ぐらい is preferred to ごろ:
“Approximately when will you come?” => “何時ぐらいに来ますか”
This example came up while doing a lesson quiz and I thought that in this case, ごろ would be more appropriate, especially because of the following grammar point from the lesson, but to my surprise the app was expecting ぐらい:
[くらい・ぐらい is more often used to describe amounts, while ころ・ごろ is almost always exclusively used to highlight a point in time]
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To follow up on the question asked by alexpwns, why is で used after くらい in these examples?
後３分くらいで着く。
どのくらいで着きますか?
あと３０分ぐらいで行きます。