What are the total yearly costs of maintaining a 30' sailboat in Chicago?
Assume I want it conveniently "parked" downtown at Monroe or Belmont Harbor
or an equivalent facility. (not necessarily at the CYC -- that's a different
question)

When people remove their boats before the lake freezes over, where to they
store them? Be sure to include those costs also.

Please make the list of costs as comprehensive as possible, even if
estimated amounts are not available for all items.

ATR -- 

Having done this precise task, I still don't think that you're going
to get an answer.  The prime reason: you want an anchorage or slip at
Belmont or Monroe Harbors, two of the places with the longest waiting
list for moorage.  LOL -- you could have asked for Montrose Harbor --
that would have been worse.

It's been 10 years since I've lived in Chicago, so here's what the
numbers were at that time -- and this is for a 36' boat with a value
of about $85,000.
*  mooring fees: $2500
*  winter storage (and outhaul): $1200
*  winterization costs depend on whether or not you'll be stepping the
mast but can be as low as $500 or as high as $2,000
*  insurance: $700
*  annual bottom painting: $500

As for winter storage, there are a huge number of options: storage on
the Chicago River; storage in Indiana; storage in Waukegan, North
Point, Kenosha or Racine.  We initially stored our sailboat indoors in
Racine; later stored it outdoors and covered it with a tarp.

Best regards,

Omnivorous-GA

Thanks for the comment... This is precisely the level of info I was
looking for... So I'll close the question now :-)