Yes, one should expect students to know that you can fit eight five times into 43, but things start being different fast when doing trickier divisions. For example take 903/13. I don't have to think to know 6 times 13 equals 78 and 7 times 13 equals 91, but the average student? Forget it.
I would be happy to see the average student take out a 5 first (903 = 50 * 13 + 253), then another one (903 = 50 * 13 + 10 * 13 + 123). From there, I would have to think a bit to realize that one can take out a 9 (123 is very close to 113). The typical student? Forget it.
And that gets increasingly difficult when the divisor gets larger. What's the first digit of 9230/131?
So, yes, this strategy isn't optimal from a # of operations viewpoint, but for many students, it probably is the best way to get an answer. What would you prefer, a student who doesn't get the answer, or one that gets the right answer in a suboptimal way?
For me, the main question is what the teacher taught: did (s)he only tell students about this slowest, sure-fire way, or did she teach them the 'right' way and told them "if you aren't sure what digit to take next, pick one that you are sure about"?