I thought this was an interesting question, although I cannot provide a definitive answer. I thought Friedel-Crafts reaction on the alcohol might be problematic (I did encounter a Russian ref to its nitration though). I thought I recalled a problem asking for the products of nitration of benzyl acetate and it was an o/p-director. I tried to confirm this, but I cannot determine the ratio of products from this reaction. It seems to be cited for the preparation of the para-nitro product.
The nitration of benzyl chloride would seem as though it may have a similar profile of an electron withdrawing chloride to counter electron donation. Again, I was unable to determine the ratio of products, but references seem as though this is used to prepare the para isomer(?).
Now, I want to take one step back and refer to the nitration of toluene. Although it is an o/p-director, the ratio of o,m, & p-isomers is ~63:3:34. Benzaldehyde gives a ~19:72:9 ratio.
I appreciate the opinion of Dan on this question and it may well be instructive, but I also think it may still be mainly an o/p-director. What might be as interesting would be the kinetics of any Friedel-Crafts reaction. Is or are they activators, deactivators, or neutral?