That would be more than welcome on AoPS, College Playground. For MO, it is hardly appropriate.

The statement is always true. Start with the fact that if the sums $\sum_{i=k}^m b_i$ ($1\le k\le m\le N$) are bounded by $\delta$ and $u_i$ is an increasing sequence of numbers on $[1,2]$, then the sums $\sum_{i=k}^m b_i u_i$ are bounded by $2\delta$. Now, split the set of indices into intervals of length $N_j$ such that the last $a$ in each interval is at most twice less than the first $a$ in each interval and the next $a$ is smaller. Let $A_j$ be the starting $a$ of the $j-th$ interval. The observation we made shows that the supremum of the sums of $\epsilon$'s over all subintervals of the $j$-th interval times $A_j$ is at most $2\delta_j$ where $\delta_j\to 0$ (tails get small). This tells us that we need only show that the limit is $0$ over the indices corresponding to the block beginnings. Now, what happens for that subsequence is that whatever product we had for $j$ gets divided by at least $2$ when we pass to $j+1$, after which we add at most $2\delta_j$. It remains to note that if you start with any number and do a sequence of steps each of which is division by 2 followed by adding a number that gets closer and closer to $0$, you will get closer and closer to $0$.