This is not an answer, but maybe it gives some insight.
I wrote and ran some Mathematica code:
k = 2;
ParallelTable[{n,
Length[NestWhileList[Floor[#/k] &, n,
Length[IntegerDigits[Floor[#]]] > 1 &]] - 1}, {n, 10^(20),
50 + 10^(20)}]
Now, in the code, I compute the number of divisions it took to result into a one-digit number. In order to do this, I take two numbers $n\in\mathbb{N}$ and $k\in\mathbb{N}$ and I divide the number $n$ by the number $k$, when the resulting number $n/k\in\mathbb{N}$ we can divide by $k$ again, but when $n/k\in\mathbb{Q}$ I take the floor-function of that fraction.
Running the code for $10^{20}\le n\le10^{20}+50$ and $k=2$ gave me the following table:
{{100000000000000000000, 64}, {100000000000000000001,
64}, {100000000000000000002, 64}, {100000000000000000003,
64}, {100000000000000000004, 64}, {100000000000000000005,
64}, {100000000000000000006, 64}, {100000000000000000007,
64}, {100000000000000000008, 64}, {100000000000000000009,
64}, {100000000000000000010, 64}, {100000000000000000011,
64}, {100000000000000000012, 64}, {100000000000000000013,
64}, {100000000000000000014, 64}, {100000000000000000015,
64}, {100000000000000000016, 64}, {100000000000000000017,
64}, {100000000000000000018, 64}, {100000000000000000019,
64}, {100000000000000000020, 64}, {100000000000000000021,
64}, {100000000000000000022, 64}, {100000000000000000023,
64}, {100000000000000000024, 64}, {100000000000000000025,
64}, {100000000000000000026, 64}, {100000000000000000027,
64}, {100000000000000000028, 64}, {100000000000000000029,
64}, {100000000000000000030, 64}, {100000000000000000031,
64}, {100000000000000000032, 64}, {100000000000000000033,
64}, {100000000000000000034, 64}, {100000000000000000035,
64}, {100000000000000000036, 64}, {100000000000000000037,
64}, {100000000000000000038, 64}, {100000000000000000039,
64}, {100000000000000000040, 64}, {100000000000000000041,
64}, {100000000000000000042, 64}, {100000000000000000043,
64}, {100000000000000000044, 64}, {100000000000000000045,
64}, {100000000000000000046, 64}, {100000000000000000047,
64}, {100000000000000000048, 64}, {100000000000000000049,
64}, {100000000000000000050, 64}}