Morgan Taylor:
I'm in a similar boat (i.e. the one about not having enough money for a retreat), and imo, this stuff should, theoretically, be the cheapest thing to do in the world.
Now, a lot of people may completely disagree with me on this, and I totally respect and understand the benefits of flying off to burma for three-month retreats; however, Buddha essentially said, repeatedly, just go to a secluded place and meditate. That costs zero dollars! And you don't have to quit your job to do it. Call me crazy, but working at Whole Foods during this time actually might be conducive to practice: it's mostly (correct me if I'm wrong) physical and does not require intense cognitive analysis, and so you could get in a lot of vipassana.
Theoretically, yes, all of us can go to a forest or a cave somewhere, forget about everything and meditate. Practically, how many of us are willing to do this? Even if we are, there are still practicalities, like food and medicine, that make this tough for the Westerner. We're conditioned to be comfortable.
Working at Whole Foods is not the same as going to a secluded place and meditating. Yes, we can learn a lot from interactions from other people, but the deepest work is when we are completely alone, without any distractions (or with a group who are all practicing silence and meditation). By the way, there are monasteries in Asia where they let people stay for very cheap or even for free for as long as you want e.g. Panditarama Forest Monastery in Burma. You just have to gather the resources to get there. Of course, there are still issues like the weather, mosquitoes, and food that we might not be used to, but we don't know until we explore.
Morgan Taylor:
That said, not going on retreat I think may definitely be holding me back. I definitely feel divided between "the world" and meditation. Retreats seem to me very much like joining a gym: technically, you can get super fit just in your living room, but joining a gym (and even better, getting a personal trainer or going to a boot camp) are extremely helpful in terms of motivation. However, many people can't afford a gym membership (e.g. me), and it sounds like in your case, you just can't afford to do a long-term retreat. The dharma is not divorced from practicality. In the words of a Thai forest monk, "I didn't learn the dhamma to become stupid." It's not like a cult that's like, give us money no matter what the consequences; we promise it's worth it. You could just go to dhamma centers (for free or donation-only) when you can to keep up your motivation. (btw, I'm in LA, too!)

Retreats are wonderful. Food is provided. Shelter is provided. In most places, basic medicine is available. We don't have to think about survival. This allows us to go deeper into meditation. The deeper we go in meditation, the more benefit we bring to ourselves and to those with whom we interact.
In my experience, going on retreat is the most wonderful thing a young person could do. It sets a foundation for the rest of our lives. Purifying our senses and perceptions when we are young is the wisest choice we can make.
Be Happy!