Deep Packet Inspection (DPI) - coping with it and/or defeating it

Question

Hi,
Now that the "DPI Genie" is well out of the bottle (or toothpaste tube) and will never go back to where it came from no matter what,
I have been looking for ways and means to:
1- cope with it when it comes time to send/rec emails of minor/modest security concern (maybe everything, since the Data Miners can be intent on seizing any/all about anyone they choose to; and,
2- for ways to defeat it when it comes time to send very confidential material (legally privileged).
I have read what I could at http://www.securemac.com/ and even though that site provides credible ideas, I believe it is the REAL-World-Users that could enlighten me (anyone) with genuine and workable solutions.
So, with utmost humility and focus, I ask those who have considered this more than just an interesting topic to please suggest/offer if you will, the most cost-efficient method(s) for #'s 1 & 2 above.
Some "joke" of a method I have witnessed is where a sender saves a Word file in TIFF and sends it as an attachment (perhaps with a pw protected file, too). Believe it or not I've seen this from a couple of gov't senders (mind you, they weren't asking me or telling me to get or use a pw).
No, the application as I see it is to send text and perhaps the odd graphic or two from me to one other; and from one other back to me. And not have either of us jump through hoops of fire or wade through libraries of "how-to" in order to do this.
For example, I've looked at some proxy site sellers of downloadable (on-board) tunnel type encryption subscriber services; and, looked at sites that say "na, just login to our proxy and to heck with on-board software sellers." -- each has its appeals and doubt-filled approach. Both seem rather price-y for a home office user over the course of 1, 5 or ten years.
So, is there a Mac OSX-friendly package or method that is not going to be cost-prohibitive? And be able to send/rec/send/rec routinely between my Mac and, say, his or her Microsoft PC?
Your direction and especially your specifics are very much appreciated.
THank you,
Max

Answer 1

Without 1 reply, can we assume everyone is comfortable with the new rules?
Someone can OPEN AND READ YOUR MAIL.
For example, See last paragraph in following link:
"Using detailed application knowledge, ixDPI can filter for an URL, an e-mail address, an attachment, a mime-type, a login, or a password. These filtering criteria can be combined to isolate specific flows..."
https://www.dpacket.org/articles/myth-7-all-ip-traffic-can-be-recorded
See the opening paragraphs of the main page (note: can "tunneling" be cracked, too?)
https://www.dpacket.org/articles/seven-myths-ip-networks-need-deep-dpi-0
Anyone running Mac's the least concerned about this?
We all know about how Comcast got castigated by the FCC, but who's checking up on them and the phone company? Even if checked on, when the "checkers" go home what then, or, how about the new business model of the commercial private service sellers (e.g., PI's for a hostile takeover monitoring executives at home or an "Extreme ex-?" like in Glen Close/Michael Douglas)??
IF not concerned, then pls suggest how a small office/home office user can also be as comfortable as you?
Again, if there is a way without paying through the nose, I sure would like some suggestions.
Thanks