I spent a few hours today dicking with my N900 and thought I’d write up some of the things I dealt with.
For a long time I’ve been using Dropbear SSH client/server on my phone, due to an alleged less-memory-usage. (When your phone starts swapping, it sucks big time.) Dropbear even supports serving SCP, but does not support SFTP. This prevents you from using any relatively-nice "file transfer over SSH" GUI, such as Nautilus’s "ssh" support or gFTP. (I think Konqueror’s fish mechanism would still work, but that is of limited utility to me right now.) It may be possible to use the sftp from OpenSSH with dropbear, but since the Dropbear packages conflict with the OpenSSH packages in the Maemo repository, that’s not especially on an N900. In fact, dropbear-scp conflicts with openssh-common (both provide /usr/bin/scp, which I think is silly, but there you are).
Of course, if you insist on using Dropbear, you can use Bluetooth to copy files over Obexftp (which Nautilus supports nicely). But since this requires Bluetooth hardware to be powered on both the laptop and the phone, I decided to replace Dropbear with OpenSSH.
Installing OpenSSH server on your N900 forces you to change your root password (the default is "rootme"), whether you’ve already changed it or not. Kind of annoying. The user account by default "doesn’t have a password", which I think means all password access is disabled. Folk wisdom suggests that giving a password to the user account "could" cause problems, but I think this is based on an (incorrect) belief that the default password is "blank" (in fact, it’s invalid, meaning there is no phone software that relies on using a password to switch to the user account, so there should be no problem with granting a password). Nevertheless I decided to just drop in a key using authorized_keys. But if you don’t set a password, OpenSSH won’t let you log in (even using publickey access); the log messages will tell you that your account is "locked". The reason is that OpenSSH looks at /etc/passwd to decide whether to let you in using any access methods at all; since the password hash is "!", it locks you out.
This page shows how to fix the "locked account" status.