I have seen outboards where the cooling passages were almost totally closed due to salt/corrosion. These were usually 1970's motors serviced in the late 1980's. More modern motors have the interior of the water passages coated to reduce corrosion.
I recommend that outboards be flushed after use IF POSSIBLE.
I have used my 1991 70 hp in the summers up to three months at a time on an Alaska trip with no flushing.
Now the motors have the flush port where a hose can be used with the motor still in the water. This is a big improvement, however the water pump and pipe up to the powerhead still contains salt water. The only way to flush the ENTIRE cooling system is with flush muffs or a tank of freshwater. The motor must be run long enough for the thermostat to open.
If the motor is used or stored in freezing conditions, the salt water will protect against freezing down to about 26 degrees F, so flushing with fresh water could be a hazard. Evinrude recommended leaving the motor down in the vertical position if the boat is in salt water during freezing conditions. The relatively warmer sea water keeps the lower part of the motor above 32 degrees. The motor should be in the vertical position for storage so water can drain out of the motor.
It is important to keep the drain holes open. When you pull your boat out of the water with the motor vertical, you will see the water drain from various drain holes. If any drains are plugged, open them with a piece of wire (a paperclip works). Even if the drains all appear open, it is possible for water to remain in water passages and can freeze and damage the motor.
In some area of the country, shops winterize motors by running them in a tank of 50/50% antifreeze/water, then letting them drain. Any water trapped then is antifreeze and protects the motor even if some drains are plugged. In the spring, the motor MUST be run on flush muffs in an area where any antifreeze will not contaminate waterways. IE: Don't run it in the lake!
Summary: Flush when you can, keep the drains open, and don't worry too much if you can't flush every time.
Larry H
Retired Evinrude/Johnson outboard mechanic