Web proxy question

I have a wireless network of about 200 users, load balanced through 6 lines using a RB493.
I’m thinking about using a PC with fast HDDs to replace the RB493 so that I can use transparent web proxy.
A few questions on web proxy:
A) Any problems I should be aware of?
B) Will sites like msn.com or cnn.com which update sometimes every few minutes be correctly handled by the proxy to show up to date info for such pages?
C) The wiki only shows port 80 cache, but can I also cache port 443 to make banking sites logos, jpgs, etc. all cached?

Ekkas

with transparent proxy, you cannot redirect port 443 - it’s encrypted. your clients should set proxy parameters in their browsers