It's fairly easy now to run headless from scratch with a Raspberry Pi.
One area that might have an issue though is debugging issues with devices that have been added to the Raspberry Pi. Often you get indication of these problems in the messages that scroll through during boot.
Are these messages echoed anywhere - to a log - or are they only available if you connect a monitor during boot?
bootlogd
will add boot logs. I did not have any boot logs on my laptop running debian-x86, until I installed this package. – ctrl-alt-delor Jun 28 '14 at 23:07