Here is the e-mail that Bradley sent me:

Jill's Progressed Chart (5.24.15)

“Not surprising to see all these Virgo planets.

First, a little over two years ago she had her progressed New Moon in Leo. This must have seeded something relative to her calling in this life. It would make sense to go back and try to tease out what seeded in consciousness at that time, for that larger calling and purpose is what will be unfolding for the years to come.

This New Moon would have been about 10 degrees Leo in the natal second house. Again we have the second house theme of being self reliant and self-sufficient in manifesting this purpose. The symbol points to finding her inspiration within (Leo 2nd).

Now, with the Venus-Mars Leo in 2nd natal, plus the progressed chart, this mass of 2nd house energy is now in Virgo. With this shift into Virgo there has likely become more increasing self-analysis over last couple years as Mars and Mercury just joined Venus in Virgo in the secondary progressed (SP) chart.

Also, the SP Moon has been in Virgo for almost the last 2 years – even more of a repeating theme of Virgo “lacking” relative to second house self-worth. Moon Virgo can also be a time of an identity (moon) crisis (Virgo), which stems back to the root lack of self-worth, self-esteem, and self-value, linked with the need to continue to liberate from all the conditioning the consciousness has internalized. There is a need to free oneself from self-measuring based on comparing and contrasting oneself and others. Others will appear more successful, more accomplished. This may be true, and it may be a facade of hypocrisy. Ultimately, there is the heroine’s call – her special calling – the timing of which has nothing to do with anyone else’s timing and path. Tuning into her own authentic (Aquarius) path (north node in ninth house) will help to secondarily her consciousness from comparing and contrasting and then measuring her own value based on a perceived lack relative to a bullshit measure of success.

Some are 50 years old and are having this exact same struggle. She is not alone. However, as you say, only she can pull herself up (2nd house planets): only she can love (Leo) herself (2nd) from within.  I suppose one thing we can do is ask the saints/Yogananda to bless her with inner self love. I don’t know how else to reach someone without the grace of the Divine working from their inside.

One other thought is that the last quarter square of Venus-Mars to Pluto – crisis in belief, relative to life purpose – is related to finding a purpose; this purpose, relative to a last quarter square, may not be fitting into consensus society. So, having these symbols wrapped up in needing to free oneself from society and social sphere defining one’s position in the word – a crisis in “what do I believe my purpose is because I don’t know how it fits into the reality I’m witnessing.” There is a need to originate this purpose completely from within, regardless of what others think, say or do.”

Edited for clarity. As far as my coming and goings with Jill are concerned, this hits the nail on the head.

And this was a more obscure interpretation from Tarek Moustafa, an astrologer in Keep It Simply Seriously:

Talk to us about bullying in school.

Which may be the result of many what the native have experienced as a child a discord between parents at home, of verbal conflicts/arguments on matters of money and acquisition.

The native may found herself encountering usually bad people (from her perspective) until she learns that the people she encounter mirrors her inner fears and insecurities.

The native should observe her progressed moon aspects to natal, and her progressed Venus direction and aspects, for they will show moments of hardships and victories in the native life.

The native needs guidance to understand relationships. i.e… other means of knowledge beside astrology.

The worst aspects of the chart.
– Chiron in her place.
– Mercury applying to oppose the conjunction Saturn/Neptune
– The angular conjunction of Saturn and Neptune.

The best aspects:
– Moon applying to Venus by sextile.
– The grand trine Sun/Pluto/MC
– Jupiter / Node applying trine.

What happened on the day of the new moon on “1-Jan-2014″ (i.e late december 2013/Early Jan 2014) may provide a clue for the native about the performance of the focal of her T-square and his Almuten figuris.”

A lot of that is Greek to me. -shrugs-