To answer the initial question: Yes it does matter. But -- the issue is complicated.

However:
At the speeds we bi-cyclists travel: More trail increases straight-line stability, decreases 'twichyness' and makes it easier to ride 'hands-off'. Reference link:
There are a couple of earned Doctorates out there dealing with the issues of two-wheeled stability.

Get onto Google/Youtube and look around; you'll probably learn more than you wanted to know. ;o)

Joe