1. Oil change/engine winterization...my mechanic will change the oil for cheap
before I sail back to the yachtyard. They charge $160 to winterize.
I paid a mechanic to change my oil the first winter and watched what he did so that I could do it myself the next time. It is not rocket science.
You will need to buy a hand pump to suck the old oil out. A good one costs about $30.
You will also need to top up the transmission fluid and remember to suck out the excess in the spring.
I believe you want to change your oil on a warm engine and then not run it again on the new oil before laying it up. I understand that the combustion products from running the engine create corrosive chemicals in the oil, which can damage the engine if it sits idle for a while.
I am not sure whether a 10 minute run to the yard will do any damage. Others will certainly correct me
2. Battery storage....do you remove from your boat? They want $45/ea to
store and load test.
A seriously discharged wet cell is likely to freeze and be destroyed by a severe Chicago winter.
If you have wet cells the best solution would be to keep a smart charger plugged in all winter (if the yard allows this -- mine doesn't). You can also take the batteries home, as I do, and keep one plugged into a smart charger and alternate batteries at the first of each month. I store them in my garage which never gets below freezing.
3. Winterize head/holding tank....they charge $30 & up. I think I can do this.
When you have your head pumped for the last time before hauling, make sure you flood it with fresh water from the shower head while it is being pumped, until the effluent runs clear. That is a great way to keep your boat from developing unpleasant odors over the winter.
4. Shrink wrap...they charge $620 (which I think is ridiculous)...should I just
tarp like crazy? What supplies do I need to do this?
Finding a tarp solution that works for your boat can be a challenge. It took
me several winters before I evolved a scheme that worked.
Are you storing the mast on the boat? Up? Or lying across the coach house? The horizontal mast can act as the ridgepole for a tarp and make the whole business easier, but it is a pain to get around on the boat over the winter if you need to.
5. Winch maintenance? Steering system tune-up? Outdrive service?
Winch maintenance is an easy spring job. You should learn to do it yourself. You can service 7 winches in about an hour once you know how to do it.