Do you recommend beginners chase cheap Upwork gigs for the first few deals or go towards more expensive ones ASAP?

On Upwork, you usually have multiple assets; your profile itself is an asset. To maximize its quality—and thus get really good jobs—for your first few deals, don't worry about making the most money right away. Instead, aim to get a couple of really good five‑star written reviews on projects between zero and a thousand dollars. That makes it far more likely you'll land a ten‑ or twenty‑thousand‑dollar project later, because on Upwork the big first filter is whether you've done work for anybody before. About 99.9% of applicants haven't, so if you're the one who has, you get consideration. It's unfortunate, but if you can get something on those small jobs—even if it takes 5 to 10 hours and you're working for the equivalent of $20, $10, or $5 an hour—you'll scale quickly. We've seen someone in Maker School do a job for $2 an hour equivalent and then land a $30‑ or $40‑an‑hour job. If you're capable of delayed gratification, you'll do well.