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pen testing beginner

hello everyone, 

have been a linux only person since before 2000 (late 2.2 early 2.4 kernels), yet haven't done much with it in the last ten years.  when i did do more with it, it was a in depth hobby that i enjoyed learning and playing around with.

now that i'm getting up in years and have beat up on my body from being a carpenter i'm looking at getting back into it and into pen testing.

from what i have been reading lately i'm going to have to know quite a bit about a couple of different things that i didn't jump to deep into before, programming and networking especially.

for the programming part--  i can read the manuals and papers on how to make programs work and change how they operate with different calls on the cmd line.  yet when it comes to writing actual programs, i.e. python, bash (not just linking things together in a script, yet writing operational parameters) i sometimes run into walls, especially with python.

for the networking part--  i know basically how machines talk to each other and basic routing, yet, i don't know about the operational specifications, i.e. osi model (which i'm reading now, as to these questions being asked), and other networking concepts, packets, priorities, cidr addressing, etc.

basically my questions are, how in depth into both, networking and programming am i going to have to delve?  i have given myself a four year window on this learning cycle and am curious about going about it.

should i learn one then the other, if so which one first?  should i learn them at the same time so that they compliment each other?  should i learn them as i read farther into the pen testing books that i have found online?

i started out with mandrake 7 and then jumped into debian (because they had the best package management at the time) and have stuck with it since.  i had a domain name, with http, https, mail(postfix), dns and such running on my server, along with a backup server and a byo firewall(soekris 4511), so i know about basic routing principles and how to set up a server to get things working properly.  right now i have a dual boot, three partition system going on, linux mint debian edition, kali linux, and a shared partition that i keep things on that i use in both, music, virtual machines, config files, etc.  i even took a linux security class back in the day.  looking at getting another domain name and building my home system(s) again.

please just give advice and not right or wrong opinions on what i maybe trying to do with my options and if i should actually take some classes to augment my self learning.

thank you.

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