s it a bad idea to use gmail to email escorts? is it equally bad to have a spreadsheet in my google docs with the escorts i want to see?

Even though Google states that the email IP is untraceable, I would not take chances, I am a customer of hushmail and I love it, their servers are located in Canada btw...regarding the spreadsheets, I think you are better off creating a folder dedicated to that purpose on your email provider's site. Remember an email means nothing but if things go wrong, it can strengthen the case and use as a supporting evidence against you and, that would be good.

It's easy to use. Go to My TER > My favorites

My guess is that I'm too small a target for LE to invest the time to get these records, but there is always a risk.

As for my records of whom I've seen, etc.  I use paper and pencil and hide those sheets in some innocuous folder among my thousands of folders at work.  It's labeled "misc stats"  and everything is coded.

While hushmail is a good option, probably better than most options, it is still not invulnerable, so try to anonymize it as much as possible.  (They have given clear text copies of email as part of a LE investigation before, although that was about a real criminal.)