I used to do all the winterizing myself. Never had issues. Attach a hose. Open the valve at the bottom of the tank and walk away. Close the valve in the spring after running some water through to flush whatever had settled in the tank. Now, I hire somebody. I like the convenience of just locking the door and leaving. I get an email in the spring saying everything works and the house is cozy. Same guy watches so there are no surprise trees that came down and fell into the living room. Anybody who goes away should have a "guy".
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