Froggy, you are right, it is a whole spiderweb if you think of it. The secret (for me at least) is to keep it very very simple. Dont go too much into detail. Only look (at least in the beginning until you feel more sure of yourself) at the major planets and aspects in your natal chart, only look at Sun, Moon, Asc., and their rulers when looking for personal or emotional change and if you want to know about career, only look at the MC and the ruler of the MC. For illness, only the 6th house ruler, the Sun (because he represents the life force) and Ascendant (physical body). Just forget about all the nitty gritty half this or semi that, points, chiron, lillith, you name it. Not necessary. You can get an enormous amount of info by just looking at Sun, Moon, Asc. and their rulers. If you want to know why you are feeling so unfocussed, just look what is happening to your Mercury or ruler of your 3rd house. Any Neptune transits? Mercury by progression maybe aspecting Neptune? things like that.
Or if you see a transit forming, then imagine what it could do to you. Best thing is to write down what you feel, the ups and downs you had so you will know what to expect the next time around
Now transits to natal is fairly easy of course.
Look specifically at aspects which repeat themselves. Take for ex. a natal Mars-Venus square. If transiting Mars goes over that Mars or Venus, you can expect a problem in the love department for a couple of weeks. Same if trans. Venus transits over one of the two planets. It will be better than Mars of course. Expect a few weeks of less problems in the relationship, especially if Venus transits Mars. If you have a Venus-Pluto aspect and transiting Pluto goes over one of the two,(I mean either by conjunction, or any other aspect) then expect a long period of slow transformation.
Progressions can be read by themselves (progressed to progressed) like a natal chart.
It shows in how far you have psychologically progressed over time, the changes you went through, the person you are now versus the person you were a couple of years ago.
Often a progressed chart later in life shows far more how a person is by then, than his or her natal chart.(unless they refused change totally). This is of course because natal planets do change signs sooner or later and their new background (sign) will colour their expression. (this is one of the things you do have to notice of course, very important. Also if retrograde planets, by progression have become direct and vice versa!). Progressed planets will also conjunct, square, trine, sextile or oppose natal planets. Heavy and slowmoving planets are the one's to really look out for. Mercury, Mars and Venus move fast and their influence only lasts for about a month or so unless they go retrograde, then it can take up to about 3 month.
When your Venus has been in Capricorn at birth up till you were 16 lets say, and then changes into Aquarius, you can expect of course a change in attitude and love expressions. You go from being shy, loyal and careful in love towards being a bit more innovative, trying out other boys or girls (I mean generally speaking for all) instead of staying with only one, you would probably become a bit more experimental. Nevertheless, the underlying natal Capricorn tendencies will always be there, you just are not
that "stiff" and conservative anymore.
Then compare the progressed planets to the natal positions as well. Again, especially note if natal aspects are being hit by progressed planets (like a progressed planet (say Mercury) is going over natal Mercury, re-inforcing natal Mercuries energies.)
Transits to progressions I would handle just like transits to natal to start with. After all, the progressed chart is how you are NOW and transits going over your progr. planets also show how you get influenced by them.
It is very difficult to get a good overall picture, even for me after so many years, but somehow, you learn to leave the unimportant things aside.
Be systematic and dont try to look at
everything. That will drive you crazy.
A good way of doing it is asking yourself questions and only look at the significators. "What are my financial prospects". 2nd house, ruler of the 2nd.
aspects to the ruler of the 2nd. Planets in the 2nd.(natal impression first).
Which slow moving planets are going to form an aspect with either one of them.(transits) So you get a bit of the feel of what is going on or what you can expect.
Then look where the progressed 2nd house ruler is now, which house, which aspects is he making. Any transits hitting him in the progressed chart as well?
Look at the progressed Moon, always, to see what could happen to you emotionally. Will you be very upset about that Saturn transit over your 2nd house ruler? Look at the Moon's aspects and transits to your Moon for that moment as well.
How will you deal with the difficulties? Look what your Progr. Sun is doing, her aspects.
Will it make me angry? Have a look what Mars is doing by progression and if he is being transited by a planet at the same time.
Bring a little discussion into your head. It is also a very intuitive thing, all this combining and you probably will feel better what the aspects are telling you.
Be patient. It needs a lot of doing and doing and doing.
Hope I explained it a bit. I am not very good at writing, but hope it is a bit understandable for you. Other astrologers might have other techniques and hopefully some of them will also come into this discussion.
Cheers, Starlink