Shopping, shopping, shopping!, Recommendations? Options

[Penta]

Okay...

After graduating college, I have a job I have an even chance of getting that'll pay (gross) in the higher end of the $9-15/hr range, low (near-zero) expenses, and $300 in graduation gift cash in bank account.

So, two things I'm shopping for, for which I'd really like recommendations:

1. A headset. PC, USB. I'll be using it for chatting primarily, but also for gaming, and for voice command stuff possibly - depends on whether I can justify Dragon Naturally Speaking as something to compensate for disabilities. It's expensive, so I doubt it, but y'never know.

2. Longer-term, a new laptop. I currently live on a desktop that's on its last legs. I need a decent machine for gaming, and the portability and privacy of a laptop have appeal when one still lives with their parents, a situation likely to continue for the foreseeable future.
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Laptop is a distinctly long-term thing: I won't be buying it til January at the earliest, I think.

Headset is more likely to be purchased soon.