No need to bleed the system.
As other suggest, leave the tank full all winter then pump out the fuel in the spring if you must. We bought a 285 in 2001. It had a half tank of diesel. It had only been sailed a couple of times a year for the previous 4-5 years. The owner couldn't remember the last time he filled the tank. It ran ok so we just topped of the tank and added diesel treatment as you suggest. The next spring it started and ran ok, so we just ran it hard, then filled it when it got low. The more it ran, the better it ran. We planned on changing filters that fall, but never got around to it. Bought Dragonfly the following spring so never had to change fuel filters and bleed the system.Bleeding the system can be a challenge the first time, but nothing to it after you have done it once. Best option is to find someone to help your change the filters and bleed the system next spring. If you don't want to change the filters, just pump out the fuel. You won't pump the fuel out of the fuel line.Good Luck.Mark