I take it you're positing these steps somewhat tongue-in-cheek, but the fact of the matter is, these are all good methods for protecting one's privacy (though the resourceful investigator might still be able to piece together some of your offline tracks). Living in this manner would not be much different than how we lived as recently as the 1980s (and some of the older among us, I am sure, still live this way).
The implication, of course, is that all these attempted circumventions in the name of privacy are terribly inconvenient – but as a general rule, I fail to agree with that argument. I am inclined to believe that many of the individuals who live in such a manner would (and do) find themselves much the better for it. No longer bombarded by information overload from digital cable or the internet, writing letters and making phone calls only to the people who really matter to him/her, taking time to actually enjoy a book, album, or drive through town; in essence, living intentionally and being able to wink at such little faults that we all have, since he/she is at peace with one's self.
Rather than see such antiquated habits as an inconvenience, I think that many of us, once we have looked beyond the haze of propaganda in modern culture, would find it a "consummation devoutly to be wished."
I did post somewhat tongue-in-cheek, but you do bring up a lot of good points. I use Apple and Google services and I am on Facebook, Twitter etc. so my privacy is already compromised. I basically have to trust those companies to keep my data secure and as we have seen Facebook has already totally messed up when it comes to securing it. However if one wanted true privacy and did not want to be "tracked" and "marketed as a product" or have any of their personal info fall into the wrong hands then going back to a pre-internet life would truly be the best option. Now of course you'd still have your data out there if you use a bank or credit cards or even go to a hospital, but you could minimize it's exposure somewhat.