Everyone is different in what they look for.

I look for curiosity, learning, drive, achievements(professional and at home), and academics (completed degrees in CS/Math are important to me). Grammatical and spelling errors irritate me, a lot. Being cutesy with resumes irritates me. Wasting my time irritates me. I am fine reading resumes that are up to 5 pages in length (but many people aren't).

* Suck it up and set up a Latex resume.

* You're not an expert - if you are, you'd not be looking for entry level positions, and you likely wouldn't be a hobbyist. You'd probably have a history of consulting in your expert field.

* You need to put titles in your positions. While useless in precision, it gives a sense of the order of magnitude of responsibility your organizations saw fit to grant you.

* "Responsibility -> Action -> Result" is a good triplet for resumes. I use it myself. I am responsible for this class of systems, I took this action set, and this is how awesome I am. You have - 'Personally responsible for over 100 servers of varying criticality, purpose, and scope, including highly critical enterprise systems.' - That says nothing to me, it's vague enough I have to ask follow up details. Give me numbers.

- 'Summer Jobs throughout high school and college followed by full time Systems Engineering training' Vague, vague, vague. Who trained you? What certs? What jobs? If it was more than 10 years ago, I probably don't care.

- 'Analytical critical thinker with outstanding problem solving skills.' Everyone says that. Show, don't tell.

- 'Professional Programming Experience'. Not the format I prefer - ymmv - but you don't give technical details.

- "Wrote 'line of code counter' programs while learning bash and python" -- erm... this is not hard enough to even mention.

- Put a bitbucket down and mention the two most awesome projects. Don't mention the others.

- 'Several programs written for assignments while in college '
Not gonna lie, but that's what every CS major does. It is not distinguishing you at all.

- 'Technical Skills' Put this up near the top.

- 'Python, Django, Javascript, Node.js, Powershell, Bash, HTML, CSS, Markdown, Git, regex' -- formatting is funktastic here. If you are not prepared to be grilled on them, don't put them down (experience talking. :D) . And HTML/Markdown are not interesting enough to mention.

- 'Technical Certifications and Education' Drop the high school degree. Same for the MSCE - I don't know of any certificates in CS worth mentioning that aren't accredited degree programs.

My conclusion: You'd be qualified for an internship or a low-responsibility entry level position. You need some polishing on professional software dev comportment, but that's to be expected. I wouldn't reject you, but you're not standing out vs. someone with no experience and a BSCS. I suspect you actually are more qualified than what your resume represents, but you're not giving me more to go off of. Anyone who can carefully hook me harder will get called before you. Take a look at Rands "A Glimpse and a Hook" for some resume advice.

Fundamentally, when I look at resumes, I look for the awesome. If you can't show off your awesome, you drop to the bucket of non-awesome resumes, and I turn my attention to the awesomes. If I have to sort the non-awesomes, I sort by demonstrated achievements + degrees.

edit, the wrap-up:

Based on this, I would not call you before a bog-standard BSCS from Podunk U, USA. You've displayed questionable judgement in a number of items on what you judge to be worth putting in your resume (A `wc` replacement? really?), and you're probably going to bring in a lot of baggage from pure IT practices, which tend to be on the slip-shod side. I'm also not going to be keen on hiring an entry level developer as a remote worker. So you're sitting near the bottom of the stack.

You might be far better than your displayed competencies, but you're not presenting that to me.