Iterations are SHA256(SHA256(...(SHA256(256 0 bits)))) with k nestings, and beginning from an input message which is 256 bits all 0.
Each hash digest is 256 bits and is a 256 bit input to the next iteration.
Bit strings are compared lexicographically, which means numerically when interpreted as 256 bit numbers (most to least significant bits).
This is a finite sequence, as there are only a finite number of hash digests (2^256 of them), but it is not known what maximum hash may be reached, nor when it is reached.
Because hash outputs are probabilistically equivalent to random values, there is a ~1/2 chance of the sequence ending at or before 90 terms, due to the underlying hash series forming a cycle. If reached, the expected value (with standard deviation) of a(90) is 2^(~128.1, s.d. ~13.6), on an underlying hash value of 2^256 - 2^(~127.6, s.d. ~13.6).
The first nonzero hash in the series, 0x66687aadf862bd776c8fc18b8e9f8e20089714856ee233b3902a591d0d5f2925, in base 10 equals 46320509353513273106582423493727320152202237096314791991810382902766530930981.