A couple of remarks: Since $p$ is odd, you might as well look at $\frac{v^{p}-1}{v-1},$ and allow $v$ to be negative as well as positive.
As you noticed, any prime $q \neq p$ which divides this quantity is congruent to $1$ (mod $p$) in partial answer to your second question. This is because $v + q \mathbb{Z}$ has order $p$ in the multiplicative group of $\mathbb{Z}/q \mathbb{Z}.$ Also, $\frac{v^{p}-1}{v-1}$ is only divisible by $p$ when $v \equiv 1$ (mod $p$), and in that case, it is divisible by $p,$ but not by $p^{2}.$ That begins to answer your first question. To continue answering your first question, I find it necessary ( at least in my own way of thinking) to use some algebraic number theory. I can't give (and don't at the moment see) a totally convincing answer, but here's some slight justification. In rings of algebraic integers,we need to work with prime ideals, not prime numbers. In the ring $R = \mathbb{Z}[\omega],$ where $\omega = e^{\frac{2 \pi i}{p}}, $ we have $\frac{v^{p}-1}{v-1} = \prod_{j=1}^{p-1}(v - \omega^{j}).$ The only prime ideal of $R$ containing the rational prime number $p$ is the principal ideal $(1- \omega)R$. We already know that $\frac{v^{p}-1}{v-1}$ is not divisible by $p^{2},$ so we can ignore this. If $I$ is any other prime ideal of $R,$ then there are no values of $k \neq j$ such that $v-\omega^{j}$ and $v - \omega^{k}$ both lie in $I,$ for otherwise we would have $\omega^{j} - \omega^{k} \in I,$ and then we would easily find that $I = (1-\omega)R,$ which we have deal with. Now $I \cap \mathbb{Z} = q \mathbb{Z}$ for some rational prime number $q,$ and if $q^{2}$ is to divide $\frac{v^{p}-1}{v-1},$ we need $v - \omega^{j} \in I^{2}$ for some $j,$ and we might expect this to be rare.
I just thought of a reasonably elementary explanation. In order that $v + \mathbb{q^{2}\mathbb{Z}}$ should have multiplicative order $p$ in $\mathbb{Z}/q^{2}\mathbb{Z}$ ( this last ring is not a field, so we need to take care). But this multiplicative group is cyclic of order $q^{2}-q.$ However, only $q-1$ elements of this multiplicative group have order not divisible by $q$. So, loosely speaking, if we choose $v$ at random, the probability that its image has multiplicative order not divisible by $q$ is about $\frac{1}{q}.$ Since we know that $q \equiv 1 $ (mod $2p$), this means that the "probability" that $\frac{v^{p}-1}{v-1}$ is divisible by $q^{2},$ given that it is divisible by $q$, should be around $\frac{1}{q},$ so certainly at worst around $\frac{1}{2p+1}.$