Well good for you, at least your business is doing good. Ideally you should service your machine every 3 to 4 months but no later then 6 months. Your group gaskets also referred as Group O-Rings will start getting hard and grooved after a few months of constant use. After about 6 months they will be almost hard as a rock. They really aren’t that fun to chisel out.
Your portafilter should be pointing towards you or a little to the right. When you start going further right is when the gaskets need replaced or when you gaskets start leaking. When you replace the gaskets it's also good time to check and or replace your screens.
If you have been keeping soft water to your machine as in 3 grains or less then it should be fine, and shouldn't need descaling. I am assuming your machine is under a year old. If your water is over 3 grains you should replace your water softener cartridge or refill your system. If you don't have one, get one. This will help dramatically increase your machines life expectancy.
