Hi-

How this happens depends on the other aspects to Pluto in your natal chart as well as those made by transiting planets. Was your Pluto well aspected at birth? ( supported by trines and sextiles) or mainly badly aspected (squares, oppositions, inconjuncts, semisextiles)? From my own experience, "living" through this transit (I almost died actually) can be rough, if you have hard aspects at birth and Pluto is annoyed by other bodies during it's transit. I have to tell you Pluto is being squared by Uranus for a long time, and will be hit by Saturn as well during that time. When Pluto was conjunct Mars in my 8th house (hah!), at an exact square of my natal Pluto, Saturn was opposing the transiting position. It was the worst time of my life. Of course it might not be "life and death" as far as your actual life is concerned, that shows in my chart, but that kind of atmosphere will surround whatever signs and houses are involved in your chart. It is very important for me to stress here that we always have free will (Although I believe a person with many hard aspects to a planet can feel "compelled" to act in a negative way). Put your efforts into making the changes that Pluto will require of you: discard the old and useless, and prepare for the new that will enter your life. Otherwise I think Pluto can be the most ruthless planet in the zodiac, and the changes will be forced. I can see that in my own case. (with Mars conjunct Sun squaring Pluto conjunct Uranus in my birth chart you can imagine that it was not a "flowing " process- and I do not think I have utterly changed).

Yes, I just invented a new aspect the "sqaure" 88 degrees and more user-friendly. If anyone can possibly teach me how to type, or even do i for me, please let me know...should have taken typing instead of band in high school. I meant "square". Must be that badly ( horribly) aspected U/P conjunction in  Pluto. These little typos drive me crazy....

When you begin to see this aspect depends on how wide an orb is used.  Robert Hand uses a narrower orb, so that the stronger effects of the transit are felt later in life.  You are probably using a wider orb, greater than 1-3 degrees.  So, you are both correct.  

Like you, when watching my own aspects, I set a wider orb (around 5-7 degrees) so that I know in advance when a particular aspect is approaching.  

Pluto sq. Pluto is an interesting transit.  Having gone through it myself, I can say from experience that it's nothing to fear or worry about...usually.  I can say that now that I'm through it, though.  At the time, I thought my world was ending, and in fact, it did.  

Pluto is going to tear down anything that isn't working and anything in your life that isn't consistent with your soul.  Pluto is similar to the Rising Phoenix.  Out of the ashes, a beautiful phoenix will rise.  

When you get to the other side of this transit, your life will be happier, fuller, and more like the "real you."  We tend to fall into patterns, out of habit and fear of change, that really aren't good for us.  Pluto sq. Pluto will take those things away.  If you are familiar with Tarot, a Pluto sq. Pluto would be the Tower card.

If you have lived your life to this point with mindfulness and having those things that you truly want and desire, then this aspect will sharpen and deepen those things so that they give you more enjoyment.  Otherwise, expect a lot of panic, things to leave your life, etc.  The areas of your life most likely to be hit are indicated by the house placements.  For example, if it is a financial house (2nd), I'd start saving up money as quickly as you can, because you'll need it.  

Yet, again, it is not an aspect to fear.  Just be aware when you start to get the full power of this aspect that it is doing you a big favor...getting rid of the stuff in your life that isn't working.