Being a monstery monk while training in career online? Is it OK to be a monastery monk (eating community gruel, etc.) but using your laptop to study for your career during half the day (instead of meditation with all of it)? Would the administrator be OK with freeloaders like that?

I would help maintain the monastery, especially if it is related to my line of work (website development, etc.). Heck, I'd work full-time for free out of compassion.

I'm thinking of asking this at a local monastery, especially since I don't care to be stuck in the cycle of apartment paying and being stuck at low-ranked IT job and being crushed by loans. I would rather take time to master certain subjects while cultivating and then come back to the city when I can achieve a higher salary to match the high cost of living as a city-dweller these days... and pay off my weighty student loans.

My question pertains to monastery in California or the rest of the US. Especially those good with wifi connections. :-D
I think it is best to ask the monastery, instead on Stack Exchange.

IMHO, may I comment on a few things:

What is one's motivation to become a monastery monk?

Monks are messianic individuals who wish to vigorously study Buddha's teachings hoping one day to attain the highest level of wisdom to be able to deliver all beings from suffering. 

Responsibility

Buddhist monks receive offerings from faithful lay people, seeking answers to solving their problems. These offerings are precious and sincere, and one should not take these offerings lightly. 

There is a Chinese saying that loosely translates as: "A lay person offers a grain of rice, such offering is as heavy as Mount Sumeru, if one doesn't attain enlightenment in this life, repay wearing your hide and horn in your next life."

Monks do not only teach people, even Devas respect and learn from highly accomplished masters.

Ksitigarbha Sutra depicted the dire consequence of stealing from monasteries, which results in millions of aeons of endless torment in the deepest pits of Avici. This is because Buddhist monasteries are essential establishments to facilitate Buddhist teaching, they contain offerings from realms in all 10 directions, from beings desperately yearning to liberate from the eternal agonies of Samsara.

A monastic life isn't necessary to attain enlightenment. In today's society lays are more likely to accomplish because today's monks have more complicated problems to help lays to solve. Furthermore, leading a monastic lifestyle isn't enough, one needs to embrace the purpose of monastic life at heart, and let go of worldly attachments and eventually leave Samsara.

Turn challenges into opportunities

Buddhists do not ask Buddha to alleviate our lives' problems. We brave hardship. We do not cut off our problems from our lives, we turn challenges into opportunities to better ourselves, turn anxiety and stress into Bodhi, and gratefully thank life when it gives us lemons.

In closing, please do not take my words as criticisms. I genuinely thank you for this interesting question that allows me to contemplate on my practice and write out this submission to help bring more clarity to my thinking. If there is anything I could improve on please do not hesitate to share your feedback.