Background:
Consider sums of the form
$$\sum_{a_1=1}^n\sum_{a_2=1}^{a_1}\cdots \sum_{a_r=1}^{a_{r-1}}{[\gcd(a_1,a_2,\dots ,a_r)=1]},$$
with $[\gcd(a_1,a_2,\dots ,a_r)=1]$ being equal to $1$ if the condition holds true and $0$ otherwise. After a bit of experimentation it appears that
$$\sum_{a_1=1}^n\sum_{a_2=1}^{a_1}\cdots \sum_{a_r=1}^{a_{r-1}}{[\gcd(a_1,a_2,\dots ,a_r)=1]}=\sum_{m\leq n}\sum_{d\mid m}\mu\left(\frac{m}{d}\right){d+r-2\choose r-1}. \tag 1$$
This method is really fast and I would love to know how to simplify this further. On the other hand we have the well known result
$$\sum_{i=1}^n\sum_{j=1}^{i}{[\gcd(i,j)=1]}=\sum_{k=1}^n\varphi(k)=\frac{3n^2}{\pi^2}+O\left(n\log n\right) \tag 2$$
which we could use to get something like
$$\sum_{a_1=1}^n\sum_{a_2=1}^{a_1}\cdots \sum_{a_r=1}^{a_{r-1}}{[\gcd(a_1,a_2,\dots ,a_r)=1]}= \frac{n^r}{r!\zeta(r)}+O(?). \tag 3$$
Questions:
1) How can we further simplify $(1)$?
2) What's the error term in $(3)$? I'm not sure what I'm doing wrong but I can get it lower than $n^{r-1}\log n^{r-1}$, which seems ridiculously high.
3) Is there anything to be found in the literature about sums of the above form?
Addendum (2019-04-24):
From A002088 we also have
$$\sum_{k=1}^n\varphi(k)=\frac{1}{2}\sum_{k=1}^n\mu(k)\left\lfloor\frac{n}{k}\right\rfloor\left\lfloor\frac{n}{k}+1\right\rfloor \tag 4$$
which we can use to get
$$\sum_{a_1=1}^n\sum_{a_2=1}^{a_1}\cdots \sum_{a_r=1}^{a_{r-1}}{[\gcd(a_1,a_2,\dots ,a_r)=1]}=\frac{1}{r!}\sum_{k=1}^n\mu(k)\prod_{j=0}^{r-1}\left\lfloor\frac{n}{j}+j\right\rfloor. \tag 5$$
Is this a better approach? Still, I don't know how to simplify the RHS sum-product.