Psalm, you asked:
am I destined for challenges every step of the way this lifetime?
Some people are more challenged than others. The more squares, T.squares and especially Grand squares as well as oppositions a person has, the more this person will be challenged, every time a transit passes over the sensitive points (Apex especially).
It becomes like a cycle. First it is a conjunction, then some years later (especially with Jupiter and Saturn which move faster than the other slow one's) a square, then again the opposition followed by a square again etc. The benific aspects also trigger the existing challenging aspect of course. Good aspects can never make a basic difficult aspect "easy". With a positive aspect I usually see more focussed energy put towards the problem at hand. Where one used to really get into trouble or hardship, one can, with a trine or sextile, get over these issues easier, handle them better.
When the planets in a T-square, by progression, get into another sign, again, the dynamics of that T-square will change for the better (if the planets are in more suitable signs) or worse.
Your chart shows a great weakness in Earth and Water whereas Fire and especially Air are very strongly represented. This in itself shows lots of versatility and change.
Your Sun, Ascendant are in mutable Air and Mercury ruling them in Libra, Air again.
The Leo planets, all ruled by the Sun also get the final ruler in Libra.
Saturn's ruler Pluto is also found in Air so everything in this chart ends up somehow with an air overtone and the rest is all fire.
Venus and Mars are placed in Water houses which creates a lot of frustration for them because they are both are ruled by Fire and the other personal planet Moon is in an Earth house where she is forced to act more earthy which is also problematic. Earth is too slow for this very curious and restless Moon.
Having that Moon in your 10th house and also conjunct the MC is a sure sign of a very restless life, lots of changes in career and social circumstances. This is underlined by the square to your Ascendant and Sun. Uranus opposing the MC and the Moon tops it all off!! I dont think you can ever escape perpetual change in your life. You just have to go with the flow and being so Airy, I think you can.
It is the planets in the 12th which seek solitude and could make it difficult for you.They want peace and quiet and are not really getting that unless you actively change outer circumstances so that you can fill up your batteries. Especially mental rest is of utmost important to your health.
Chiron, the one you want to hear about so badly
is actually not at all an easy one for you to have there. It often shows a person who seems to feel completely alien from others when in a social situation. It is almost painful to have to act "socially" and others might also find the person very different in some respect.
This Chiron position can cause a lot of emotional pain.
I want to ask you what that green "Venus" at 17° Aquarius and the red "Venus" (Lilith?)at 6° Capricorn represent. I have never seen this before. Is one of them Ceres?
It is a bit confusing to see three characters in the form of the Venus glyph.
And what is the "Mars" at 19° Leo? I used to have WinStar, but never saw these glyphs.