You don’t understand. If your element has two connectors but not at cables but at its PCB then they both are ‘one insertion’ so one footprint.
I started to assemble SMD myself around 1992 and till now I don’t have microscope. When I started to have to use glasses for reading I have bought a workshop lamp with magnifying glass.
I have no space at desk for station so I use:
Not needed. I think.
I use 0,5mm tin with rosin and metal container of 8mm film with rosin dissolved in it.
It was very expensive when I started to be interested in electronic so to have one I had to do one myself. Now enough good (as for amateur needs) digital oscilloscope is rather cheap. And you can also use USB oscilloscope adapter that is even cheaper, I think.
No!
First silicon transistor I have ever had in my hands costed 3% of my father month salary. Now BC547 is about 0.004% of typical month salary (here in Poland).
Try workshop lamp with magnifying glass first.
Here is fragment of picture we put into our documentation. We have never send any KiCad files. Only gerbers (+ drill files) needed to manufacture PCB (fabrication, courtyard are not needed for it) and P&P files needed to program assembling machine. The rest is in form of pdf containing BOM + needed comments and remarks + pictures like this one (second is the same but with values, but I think they don’t need it). We have never send them any schematic of our devices.
You see U5 first pin. In diode box I add one line as cathode marking.
Try to do it with QFN package 
As you see I use light gray with copper at my pictures. It can be difficult to find rectangular pad at it, specially if it happens to have there some text.
My manufacturer don’t get courtyard. He only get a picture. You can mark the whole module as M1 and one connector rectangle as S1, and second as S2 and write in text that M1-S1 and M1-S2 are the sockets listed in BOM pos.32.
And generally you are right. But I use courtyard a little different. I do it only because there are no free layer pair to be used by user.