So there’s this sweet domain name I want that expires next month. It’s owned by some random dude and looks like a geocities site.
With this barely useful amount of information, would I be better off making an offer for it, or waiting for it to expire and hope I snag it for cheap?
Make an offer. Most domains automatically renew so it probably won’t expire and give you a chance to grab it.
By the way, what’s the domain? 
Stick it on your registrar’s watch list and wait for it to expire. In my experience, absurd amounts of people don’t auto-renew / leave expired card details with the registrar / register for ten years and then lose access to the administrative contact email address, so you might as well have a stab at it. If it does auto-renew, then you make an offer. Start low! Is it a real personal site, or a domain squatter?
A very small, personal site.
Thanks for the advice, both.
Who’s the registar? If it’s 1and1 or GoDaddy chances are it will auto renew
You should wait anyway. If you make an offer he’s apt to hold up. Domains are pretty cheap, 1and1 renews for $8.99 a year, so it’s no big deal to sit on a domain name forever.
But I would wait, you can always offer AFTER the renewal and they can transfer it over then