There is a question: If integers $a$ and $b$ satisfy the following properties: for any $a$ real numbers, we can do an operation to average $b$ of them to the same quantities, and we can do a finite number of operations so that all does $a$ real numbers are the same (does not depend on the amounts), we call $a$ can be averaged by $b$. We omit the condition that $b\le a$ for convenience.
(Intuitively understanding: for any $a$ cups of water with arbitrary amounts, we can do an operation to average $b$ of them to the same quantities, and we can do a finite number of operations so that the amount of water in those $a$ cups are the same.)
A necessary condition is that if $a$ can be averaged by $b$, then for any prime $p$ that $p|a$, we have $p|b$. This is easy to prove: suppose $p|a$ but not $p|b$. So $p$ will never appear in the denominator if the starting configuration is one $1$ and others are $0$, and it will never be $1/a$ for all the real numbers.
Now we seek proof that this is also a sufficient condition, but this is false. For example, $8$ can't be averaged by $6$, because if the starting configuration is two $3$'s and six $-1$'s, all the configurations it can achieve will be $x,y$ and six $z$'s such that either $x=y\ne 0$ or $x$ and $y$ has a distinct power exponential of $3$.
(Clarify: It means if you factorize $x$ and $y$ into primes (say $x=\pm2^{p_2}3^{p_3}\dots$ and $y=\pm2^{q_2}3^{q_3}\dots$) Then either $x=y\ne 0$ or $p_3\ne q_3$. This can be proven by using induction. After proving this we know that we will never reach $x=-y$ case and thus we will never have $8$ averaged by $6$)
So how to find all pairs of $(a,b)$ such that $a$ can be averaged by $b$?
The question part ends here, the followings are partial progress on this problem. To make it not seems to be too long (it actually is!), I am going to hide them.
Here list some of the properties:
1. If $a$ can be averaged by $b$, then $ka$ can be averaged by $kb$.
2. If $a$ can be averaged by $b$ and prime $p|b$, then $pa$ can be averaged by $b$.
3. If $a$ can be averaged by $b$, $b$ can be averaged by $c$, then $a$ can be averaged by $c$.
4. For $1\le x\le y$, $y^2$ can be averaged by $xy$. (it is generalized by the lemma in the answers below: if $ax$ and $by$ can be averaged by $xy$, then $ab$ can be averaged by $xy$.)
Some sporadic positive and negative results:
positive results (not genarated by the properties above):
$(16,10)$, $(32,14)$, $(27,15)$, $(64,22/44)$, $(64,26)$ etc. holds. All $8k$ can be averaged by $6k$ for $k\ge 2$. Notice that $(54,48)$ can be done (refer to the comment).
negative results:
see the answer below. Currently (tested for all $b\le 50$) there is no negative results that does not violate the necessary condition and does not satisfy the condition of the answer below, except $(64,50)$ (this one I merely think they can't do, but I don't have any proof.)
Also a result:
using the properties above, for any $b$, there is finite number of $a$ such that $(a,b)$ satisfy the necessary condition but $a$ can't be averaged by $b$
A (maybe) simpler/intermediate question: if we only consider the starting configuration with one $1$ and others are $0$, what are the possible $(a,b)$'s? Also, if $(a,b)$ can do with the starting configuration with one $1$ and others are $0$, will it be done for arbitrary initial amounts?
a sufficient condition: If $(a,b)$ satisfy $\lfloor a/b\rfloor = k$, and $k(k+1)<b$, then, if one $1$ and others $0$ can do, arbitrary amount can do. Actually, we only need $k\times (b\mod k)+(a\mod k)\le b$ is okay.