Definitely Craigslist
CL, CL, CL all the way for buying bikes - it has completely supplanted the formerly $5B USD classifieds market, and it is the absolute #1 option for placing ads - everyone uses it.
As far as insurance - shop around! Progressive is a company that advertises heavily, but I've often found that they are pricey.
Try esurance.com, State Farm, and Allstate as relatively cheap providers. There are sites such as netquote.com and insureme.com that can get you quotes from multiple providers.
Always remember - The upside of the USA being so litigious is a proliferation of insurance options.
Note that different states have very different sales taxes (i.e. Oregon) which can save you a lot of $$$ when registering the bike at the DMV.
Also note that different states have different policies on same-day issuance of new titles - in California, they mail it to you (takes about a week); others issue the same day.
Every state has its own DMV website and can answer questions by phone.
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