Cartoon Illustration Based on a made up character

Job ID: 34576870

Budget: $10 – $100 USD

I'm looking for someone I can work with on a regular basis (+/- 4 illustrations per month),
to design t-shirts around 1 character similar to the image I sent you.
the theme will be mostly self (as in me) deprecating humor
the copyrights will be mine and I need and easy to edit source file PSD or AI

can you quote me on recreating this image with the following changes.
1. ideally I would like the main character "Jack" (an alter ego when I was in University) to look more like me in a silly way. if you want to see a pic of me: https://www.linkedin.com/in/carlos-cruz-2794852a/
2. solid background (that will contrast well with black) does not have to be perfect geometry, i.e it does not have to be square, it could be part of the design, but it has to be solid.
3. shave off the mustache as I no longer have a mustache
4. put the Title (Casual Friday For The Remote Worker) at the top
5. add a window with a passerby doing a double take (doesn't have to be very detailed) Jack will always be the center of attention.
6. all illustrations will have this sigh at the bottom where Casual Friday... is now, in similar sized font: "Porra Caramba, Estamos Fudidos" (no quotes)
7. all illustration will include the brand name using a small font: "Khaos Gear" (no quotes) at the very bottom
6 and 7 will always be the same in all my illustrations
thanks!

please note, in the budge section I don't have a particular budget in mind and I didn't really know what to put, just give me a quote this is why I gave you a general example. I've used another web site, but I was never happy with the results so I'm trying freelance.