through the mechanism i don't see how this wouldn't work.
Yup... It seems plausible to me too.
is it possible to do a friedel crafts reaction on an aromatic compound such as benzyl alcohol?
or on phenylacetic acid (i.e. PhCh2COOH)?
Friedel Crafts reactions can't take place when you have deactivated systems. But the compounds that you mentioned aren't deactivated to such a great extent that the aromatic ring cannot be alkylated/acylated.
Please correct me if I am wrong