Maybe I should mention transiting Pluto was in my 1st House, and another "minor detail" would be natal Pluto in the 10th House, and another "minor detail" would be natal Moon in exact opposition to natal Pluto....
I have a somewhat different view on this. My thinking is that IF one is already quite plutonic by nature, a Pluto transit will make little or no effect on the native's life. It is kinda like being born with a red bulb on your head, every day and everywhere you go will always be red, and you will not notice anything different. However everyone else can see the red bulb on top of your head except you. It appears Bob has Pluto conjunct an angle(Midheaven),which means he may already be familiar with the energies of Pluto and may even be experiencing a mastery of it.
My husband has a Pluto ascendant, his pluto square pluto was a breeze - in fact he got the highest promotion of his life when he had it.
However mine was the opposite. I think If you are unfamiliar with the energies of Pluto like I was, a pluto square pluto may come as a shock to your entire system. I am currently getting to the end of my pluto square pluto and I can understand why this transit is one of the most feared ones.
There were some good parts to it though - as I found myself moving from the UK (London) to New York and beginning my life and career from scratch in a completely new field.
Before I made the decision to relocate, I just found that nothing in my life seemed to work any longer. Before the exact square began, when Pluto transited my descendant at 0 degrees, I basically lost all my so-called many friends and also experienced the sudden death of my sibling. (I have natal pluto/mercury) however in this same 7th house pluto transit (some degrees in) was when I found and married my husband.
With the pluto square pluto, I noticed that when I tried to do things in old ways that I was used to, I felt blocked, as if something was intentionally stopping me from proceeding. It made no sense. Saturn would automatically be the first suspect when experiencing blocks of any kind but this was a different kind of block. I searched transits upon transits to understand this and tr pluto square my natal pluto (in 4th/5th house) is what seemed like the culprit. After some much needed introspection, I realised I had to start shedding lots and lots of baggage, especially family enmeshments. It was painful, it was scary, my decision to withdraw felt like death to some family members, it was tough but soon I started to feel lighter - and in here laid the gifts.
I delved deep into the parts of me that I didn't even know were there, and I must say, the transformation is felt almost instantly by even those who didn't know me before the transit.
The part of ALLOWING the old things to die was what led to my decision to leave the UK - without the pain that came with this Pluto sq Pl transit, I may never have event thought about it.
I notice that when I try to go backwards, i.e do things the old or familiar ways, I encounter painful experiences especially from my past, whether that be people or approaches. I started to notice this, and started working on killing habits. It was like learning how to turn off and on a new switch to discover new ways to carry out same intention, and I notice then that they work beautifully, empowering me in the process.
I urge those who are confused not to dismiss Pluto entirely. Traditional Astrology is good for the insight it once provided and continues to provide but we are now living in a new age of Ascension. And as the ascension energies continue to hit us down here on earth , the vibration increases to push us more into higher evolution; things that were once hidden to the the Sumerians, the Babylonians, the Greeks and Romans are now being made available to us - the veil is thinning - dear friends, we are living in one of the most interesting times to be alive and to have the gift of astrology to decode all of it.
Stay open and be ready to adapt not just to the transits but to new discoveries, whether they be new planets or new insights into how to delineate and understand your astrological charts and your own life better so you can understand and participate in the life role you have come down to earth to play. Namaste.