If you only want to ssh to the Pi, then you don't need to connect an HDMI monitor, and you can still run a graphical desktop when you want by using a free VNC client such as RealVNC on a Windows box.
It's best if you have a fixed IP for the Pi - I have 192.168.1.5 for the wired ethernet and 192.168.1.8 when the Pi is connected via WiFi
sudo nano /etc/network/interfaces
iface eth0 inet static
address 192.168.1.5
netmask 255.255.255.0
network 192.168.1.0
broadcast 192.168.1.255
gateway 192.168.1.1
iface wlan0 inet static
address 192.168.1.8
netmask 255.255.255.0
network 192.168.1.0
broadcast 192.168.1.255
gateway 192.168.1.1
I think maybe ssh is enabled by default now, but on the old Debian release you had to do this just once to enable it:
sudo bash
ssh-keygen (press enter three times to accept defaults and blank passphrase)
service ssh start
sudo update-rc.d ssh defaults (this makes the daemon auto run at startup)
From Windows, I use PuTTY to ssh to the Pi for a console. To use a graphical desktop you need to install vncserver on the Pi; you only need to run the following two lines once
sudo apt-get install tightvncserver
tightvncserver (supply password twice, No to 'read only' password)
Then whenever you want to fire up a graphical interface you first enter the command on the pi (via ssh I guess):
vncserver :1 -geometry 1360x768 -depth 16 -pixelformat rgb565
(I made a script for this so I don't have to type it in each time)
You then use RealVNC viewer to connect to 192.168.1.5:1
It works surprisingly well - fast and slick. Better than cluttering up your desk with two keyboards, mice and monitors when you need to have a full sized PC running too.