This isn't true. Take 9_A = 1001_2. 28_A = 11100_2, which is 5 bits long (3 set). The biggest number in this path is 52_A = 110100_2, which is 6 bits long (3 set). 5 ≯ 6, and 3 ≯ 3: neither of my interpretations of your statement holds.
11100 == 111 == 11100000000, in terms of the next odd iteration
Even numbers don't really count in the process surely? All collatz does is essentially ignore those zeroes
Plugging in values from OEIS A006884, it looks like the maximum ratio between the maximum and starting values goes down until around 4255, then picks up again, gradually increasing from there. Eyeballing the growth rate, I suspect there's a counterexample to this interpretation somewhere before 10^1000. (Does anyone have an element of A006884 greater than 2358909599867980429759? That's 140 bits maximum to 71 bits starting.)