I love the Debra Silverman videos! Challenges.. hmm.
The Sagittarius aspect of being over indulgent with food & pleasurable activities is definitely a challenge of mine. The rest of the qualities tend to be attributes and not challenges, philosophical, truth speaker with tact nowadays, do love to travel but tend to stay in one place now and deal with stuff as it comes up.
The Leo aspect, I guess I do tend to act in ways to gain favor from people, I feel hurt if people do not react to me nicely and I go out of my way to be polite for this reason, I can be extravagant with myself & others materially & emotionally but more in the way of food & pleasure than material items or vanity. I overextend myself I think that is a big challenge - because I have the potential and ability but not the resources.
The Capricorn aspect, the dourness of Saturn comes out in depression but the rest of it seems to be in my favor. I am practically minded (pragmatic mystic is one term I use) but tend towards emotional expression.
Gemini Rising/Jupiter Conjunct; is spot on, the expansive messenger. I write, I talk, I tend to have friends that are separate form one another with only me as their hub. One challenge I think may be my friends view me as being very self-sufficient, BIG, and I find that when I need support they aren't around. Not sure if that is this or not...
I haven't paid much attention yet to NN and the Aquarius calling Midheaven in my chart yet. Yes, people do project on me and no I do not enjoy it even when it is flattering, I do concern myself with my own view of myself, I am a humanitarian and am very interested in human rights - particularly in the domestic violence & sexual assault sphere - but also homelessness and spiritual spheres, I tend towards warm heartedness but often like to do it from farther away which can cause me to appear cold - too intelligent comes up, or rather that I think I am too smart while intelligence is important to me, it's just an accident of birth, I like to read & write - and the shadow aspect, yes, I do mean well but sometimes people do not take me the way I intended.
Scorpio NN, I am on a journey towards wholeness that has taken me to some very dark places (one of the reasons these transits concerned me, ready to be in the light), I'm not interested in material things or possessions, I tend to live by the belief that if I see something negative in someone else its something in me I need to look at, I do truth speak, but with tact, being lazy is a challenge... not concerned enough with material things and content to get by.
6th House NN; I have always been interested in spiritual matters but not normal ones - organized anything has never worked for me, I do need to exercise more discipline and manage my time better, I do like to spend time alone which can make my social anxiety more pronounced, I do not mind tasks, I do often feel let down by others but I view that as times when I should have the inner resources to support myself, I am insightful, and have developed healthy boundaries with others - but I am horrible about routine & discipline.
Sixth house work & service; I volunteer right now but I do not work, before I went back to school I tended to work in office positions but I always felt a natural calling to help people in their healing process - to the point where I would bring people in to my personal life & my home to help them (now I volunteer and do not do that anymore). I am going to go back to work in offices but am hoping to work in a nonprofit that is of service in some way (people, pets.. anything of service & humanitarian) - I decided I do not want to be paid for or committed to full time counseling - I do what I can when I can. I have thought throughout my life that I would have made a great nun or religious leader if I had ever found an organized one that suited me - instead I have my own path which is individual & eclectic.
Okay.. I hope that helps, and that I haven't written too much. I am on my way to bed but wanted to reply before the end of the day. I have much to think on. I'll look this over tomorrow and see if I can make it a bit simpler if you haven't looked at it yet. Again thank you so much for your time, I really appreciate it.....