Spark, dont bang your head. It is really not difficult. The progressed chart by itself just shows clearly how natal planets have progressed .
Lets say at birth your Natal Sun was in Aquarius at 15° (just as an example) and at age 29 you see it has progressed into 14° Pisces. In fact at age 15, it already entered Pisces.
This you can see for every planet. Only the moon is different from the others because she moves fast, 1° per month. Even so, when you draw your progressed chart on your 29th birthday, you see your Moon somewhere in a sign or house. Every 1°-1.5° it will move further per month, so in about 28 degrees it can already get into a new sign /house. All other personal planets need about a year.
You can look at a progressed planet as a new natal planet for that time in your life. Only during a few years, not much will change, because everything just moves 1 degree up.
Now this progressed chart shows you also the
progressed housecusps which are not shown (exc. Asc./Desc. and MC/IC axis) when you take a natal chart and then have the progressed planets put around it.
So for me, the progressed chart only serves me to look at
longterm changes. When a natal planet is at the beginning of a sign, it can take almost 30 years to get into the next. When it is at the end of a sign, you can expect it to enter a new sign maybe already at the age of 2 or 5. This will show you that part of the natal energy expression of this planet will now also get a bit of flavor of the new sign. Going from Sagittarius to Capricorn for instance, will not take away the basic Sag. optimism, but will make this person a bit more careful and serious (Capri).
I therefore use the progressed chart only to look at:
1. the progressed Moon's placement,
2. to see if some planets, by progression changed to retrograde or natal retrograde planets moved to become direct,
3. to see if they moved house, so only when just entering a new house. This will show that the natal energies which were first focussed on the house before that, will now be applied more consciously on the next house. So a natal Mars in 1 (doing things for yourself), entering the 2nd house, will make you do more things in order to make money or to boost your selfconfidence. In house 3, that Mars can become more assertive in communication. etc.
4. To see if the progressed Moon aspects any other progressed planet
5. To see if any progressed fast planet aspects another progressed slow planet
From the progressed positions around your natal ring, you can see which progressed planets make aspects to your natal angles or planets.
I also see if the progressed Angles are getting into a conjunction or other major aspect with a natal planet.
If i wanted to see my life in this 29th year, what would i chart?
Both. Just the progressed, to see how you psychologically have grown and changed and the natal chart with the progressed positions around it to see how progr. planets are influencing your natal chart right now. And you can do a Solar Return for just this 29th year, based on the transits of the birthday.
Hope this is a bit clearer now.