You would do well to define exactly what you wish to hunt - which market vertical, for instance - and then make a list of domains that might serve your needs relative to that vertical. "Browse to" those domains to see if they are a website, parked or simply sitting registered yet unused.
Once you have determined your domain targets and whether they might be available (undeveloped) you can make your offers or inquiries in whatever manner you choose.
To approach the issue in the manner you have described seems a bit likely to lead to much time wasted.
$5,000.00 will likely get your a 2 or 3 word domain with some slight traffic of no particularly great value. You might get lucky, but luck is usally the product of a great deal of work.
Unless you have your heart and soul set on example.com, search around for variations. examples.com , examplesonline.com, myexamples.com, and so on.
As for comparison shopping, that all depends on where the owner has them for sale. You might not be able to compate domains from siteA and siteB, your best bet is if the owners have them listed on the same site.
IMO - your best bet is to shop around, but don't forget drop-name and backorder services, plus just for fun, see what's out there for unregistered domains, you might hit gold one day for a simple registration fee.
