Which way do you number the symbol when you are drawing it? For example am I numbering it looking at it face on or from the backside of the connector? So with the 62 pin, if I starter from the bottom left, what pin am I looking at on the schematic or does it matter?
Also, does my spacing on pins matter at this point or is that more for the footprint?
No need to draw it all as one symbol. For schematic legibility these can be broken up and numbered ANY way you like. The symbol pin number however MUST match the correct footprint pin number.
On the DB 37, it looks as though each pin is made of two parts. How do I make the pin part? I can find the part that says passive with the line but not the colored dot with the line.
I am in that box but I do not see a male pin to attach to the passive stub.
Also what is number of units per package?
Should I use passive or bi-directional?
Units per package depends on how you want to break up the package in your schematic. Do you really want ONE big connector or does it make sense to break it up into different units for different parts of your schematic for legibility purposes?
Start here:
Not sure if this is covered in the tutorial:
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Putting on my pedantic hat here… 
There is no such thing as a DB-62. The B shell size for the D family is only standardly defined for 25, 44, and 52 pin variants. I think you really mean a DC-62 (which is the high density variant of the normal density DC-37). See this Wikipedia page:
The KiCad standard libraries (as distributed with v5.1.6) makes the “error” of calling all D-sub connectors “DB#” regardless of the shell size. (I put error in quotes because the common usage doesn’t follow the original specification…)
Feel free to go back to your original conversation. 
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I can take pedantic. I knew DB wasn’t the correct description for this unit but wasn’t sure what exactly it should be. Thank you for the correction. Carrying on.
Is this where you would use “3 units per package”?
That would make sense to me.
I agree, except for specialized usages where one would group pins by function (or by what pins are needed on a particular sheet in a hiearchial schematic), breaking it out by row makes the most generic sense.
Oh, I noticed a copy-paste error there @jos. On your A and B parts you forgot to add the internal graphics. I know this was probably just a quick and dirty example to help @bwilliams60, but if you ever plan on using that symbol you may want to add that small (aesthetic) detail.
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@SembazuruCDE, are you referring to the missed connection on pin #1, 22 and 43 or is there something else I am missing?
Also, how did you make the circle inside the symbol (female terminal?) and if it was male, how would you fill it?
I am looking at the circle function but when I use it, the circle comes out rather large.
Since that connector consists of three physical rows it somewhat suggests a three unit part as an initial approach,
Well spotted 
The properties of those graphical elements for the 20 contacts can be set common to all units, however the remaining two for units A, B need to be by themselfs.
Actually, I had missed that until you pointed it out. I was referring to the missing line and circle on pins 21 and 42. Those bits are aesthetic only. Jos changed the grid TEMPORARILY to draw the fancy pictures. If you want an empty circle, you can edit the circle properties to remove the fill. As to changing the graphic circle based on connector gender, that is up to you. If you want to match the style of the standard libraries they have male pins with circles filled with foreground, and female sockets with circles that aren’t filled.
So you don’t get even more confused, those circles that you see on the pins in this screenshot:
Those are the connection points of the pins, not graphical circles. I.e. when you draw your schematic that is the end of the pin that you want to connect the wire to. On the schematic, you should see that open circle until you connect a wire to that end. (Unconnected wire ends on the schematic will have a small square the same color as the wire.) Once you connect a wire to the pin (or place a no-connect symbol), that small circle will vanish letting you know that you have made a connection there. Or in the case of the no-connect symbol, you’ve verified to KiCad that you intend for the pin to float. If you see a small green square overlapping a small dark red circle where you are trying to connect a wire to a symbol you will know that no actual net connection will be made there when exporting to the PCB. Likely you have a grid problem (see the note below).
A big note about drawing schematic symbols and the grid. When placing the pins for your symbols you MUST place them on the same coarse grid that you use for drawing the schematic. Currently, EESchema requires that wire ends and pin ends be within 0.001mm (I think, could be wrong, but it is very close) to make a net connection. Unfortunately, there is not yet any sort of object snap in EESchema, so you must rely on the grid snap to connect wires to pins. EESchema defaults to a 0.05" grid out of the box so the standard libraries are designed to either a 0.1" or 0.05" grid (smaller grid only if necessary for spacing).
Okay here is what I have so far. Is there a way to connect these wires without the mess or am I going to have 62 wires running on this schematic. Also, what about the right size where it goes outside the frame? How do I fix that?
Try flipping your connector vertically to make the routing easy, or make use of the local labels to name your pins, less clutter but more typing.
Would it be better for me to put more pins in each row? It is only the schematic right? Placement is more for the PCB section??
Are you aware of labels? In a lot of cases these make it a lot easier to get a readable schematic for such high pin count components.
