Erdős, Granville, Pomerance, and Spiro [EGPS90] have proved that the answer to the first two questions is yes, conditional on a form of the Elliott-Halberstam conjecture.
It is likely true that, if $k\to \infty$ however slowly with $n$, then for almost $n$ the largest prime factor of $\phi_k(n)$ is $\leq n^{o(1)}$.
The number of iterations required is A039651 in the OEIS.
That is, there is (eventually) only one possible sequence that the iterated sum of divisors function can settle on. Selfridge reports numerical evidence which suggests the answer is no, but Erdős and Graham write 'it seems unlikely that anything can be proved about this in the near future'.
Can one show that there exists an $\epsilon>0$ such that there are infinitely many $n$ where $m+\epsilon \omega(m)\leq n$ for all $m<n$?
Erdős also believed that $\Omega$, the count of the number of prime factors with multiplicity), should have infinitely many barriers. Selfridge found the largest barrier for $\Omega$ which is $<10^5$ is $99840$.
In [ErGr80] this problem is suggested as a way of showing that the iterated behaviour of $n\mapsto n+\omega(n)$ eventually settles into a single sequence, regardless of the starting value of $n$ (see also [412] and [414]).
Erdős and Graham report it could be attacked by sieve methods, but 'at present these methods are not strong enough'.