For decreasing positive integers $a_1>a_2>...>a_n>0$ when $a_1=m$.
Mark $a_{n+1}=0$, Prove that $\sum_{k=1}^n \frac{a_i-a_{i+1}}{a_i} < H_m=\sum_{k=1}^m \frac{1}{k}$
Might add that $n$ can be chosen by us, as long as $a_1=m$.
I got the problem from a different problem and if I prove this I solved the problem, so I'm not sure if it's true.
I know the harmonic number is achieved if we choose $a_i=m-i+1$ i.e $a_m=1<a_{m-1}=2<...<a_1=m$
My attemp was to prove that the question is equivalent to proving $$\min \sum_{k=1}^n \frac{a_{i+1}}{a_i} $$ is achieved by $a_i=m-i+1$ i.e $a_m=1<a_{m-1}=2<...<a_1=m$.
Showing the equivalent is simple, but proving that this is the best I havn't manage to do.
The idea has been nicely demonstrated in Matija's answer. Here is a formal proof for the general case.
For $1 \le i \le n$ and $a_{i+1}+1 < k \le a_i$ is $1/a_i \le 1/k$, so we have $$ \frac{a_i - a_{i+1}}{a_i} = \sum_{k=a_{i+1}+1}^{a_i} \frac 1{a_i} \le \sum_{k=a_{i+1}+1}^{a_i} \frac 1k \, , $$ with equality if $a_i - a_{i+1} = 1$, and strict inequality otherwise.
It follows that $$ \sum_{i=1}^n \frac{a_i - a_{i+1}}{a_i} \le \sum_{i=1}^n \sum_{k=a_{i+1}+1}^{a_i} \frac 1k \overset{(*)}{=} \sum_{k=1}^m \frac 1k = H_m \, . $$ $(*)$ holds because every integer $k$ between $1$ and $m$ is in exactly one half-open interval $(a_{i+1}, a_i]$.
Equality holds if $a_i - a_{i+1} = 1$ for all $i$, that is if $n = m$ and $a_i = m+1-i$ for $1 \le i \le m$. Otherwise the inequality is strict.