Hello willcapellaro,
First of all, thank you for the presentation of your workflow. It is always interesting to read how others approach certain problems.
Now I would like to answer your four questions.
A bitmap image to trace for a pixel font in Illustrator should have the following properties:
• 300 dpi (if it has a lower resolution, then enlarge it in a bitmap programme, but the edges must remain sharp. So use for resample »Nearest Neighbor (hard edges)«.
• PNG or TIFF is a better file format than JPG.
Place the image into AI and use »Image Tracing«.
I use the following settings for this:
- Preset = Black and White Logo
- Open Advanced
- Add the mark to “Ignore White”
If you leave the white background as part of the letters, Fontself will create a coloured font. Only with pure black letters you will get a monochrome font. Therefore, remove the white beforehand. You can do this by forcing the image tracing as shown above.
I always put the elements of a letter together as a compound path. For this I use a self-written Javascript that uses the name of the top element for the name of the compound path. This saves a lot of time 
(I just noticed that the Javascript is not yet published on my Behance account https://www.behance.net/jensulkriebel. I will do that later). I will do that later).
There is a trick in Fontself to make a font correspond to the size of 12 pt. Use a square as the very first character that has a size of 70 % of 12 pt. This has been explained several times in the forum, see
Did you read this? Create a vector font in Photoshop, step by step | Fontself Maker Help Center
So far for my answers to your questions.
Have a good time.
jens