I had great responses with this method, as long as you contact them well before you're planning to apply.
First send a greeting/inquiry email. Like, "Hi, I know you're super busy but I'm a potential applicant and really interested in your school. would someone be able to look over my transcripts with me?"
If they say yes, then you can send the documents. If you go for a tour, you can schedule a meeting then. If you cant go there, you can email a PDF.
Just try to be really polite, grateful, and concise. And be willing to take a NO. Try not to let the exchange drag on and on.
I was able to interact with 3 medical schools this way and got a lot of great advice and insight last year. I even have an interview at one of them now!
With regards to who specifically to contact, just use the
[email protected] address, and don't go looking for the dean or some specific person, unless you have their card from a career fair or conference or something.
Good luck!