Apologies for the misdirection but there were buried testers in that post.
I shall illuminate as I go.
None of the embarrassments are any issue anymore. Interesting observations, Xander - I'll give them a thought. Still, being open about the issues isn't very indicative of my type, because I consider them as amusing or endearing more than anything else at the moment.
The choice of words (amusing, endearing) would be more indicative of an ENFP to my eyes plus not being defensive about failures and kind of laughing, shrugging and going "well, you know" is also more like the ENFPs I've known than most other types, well except ESFP and ESTP but I don't think you're considering those at present are you?
Yes of course
Always and ever in reference to probability.
I'd like to think that I don't ever really judge, merely analyse the probabilities and act accordingly.
Probably fail miserably though
I've long thought I'm a particularly badly definable person in MBTI, having many traits of ENTP,ENTJ and ENFP, even some INTP and ENFJ. I don't let my life depend on closure on this subject, so no worries, mate

I'm perfrectly fine with ambiguity now that I've placed less importance on personality type and more on my actual life.
You sound more ENFP from this too. Basically you make some movement toward "thinking" types but it seems more of an off handed gesture. I@d expect and ENTP to go more for the "logical" types.
Oh and ENFPs and ENTPs tend to claim that they cannot be "pigeon-holed" and will rattle the bars as it were. They are all possibility and being typed seems far too final for their ever shifting nature.
And failed miserably!
I bet you learned a lot. Wish I had the cajones to do likewise.
I've had this conversation with an ENFP before in fact. Kudos for trying, screw if it was considered a success or not.
Anyhow I'm developing a bias now so I'll shut up and see what you reckon.