I'll definitely take any info on Olson or any other time-share systems in the Chicago area. Already looked at SailTime and Pinnacle, they seem pretty damn expensive for what they're offering.
Is time-share expensive? I was a Pinnacle customer on a Jeanneau 40 out of Belmont Harbor during the 2011 season. Let's do the arithmetic:
Owning a Boat: A slip in a Belmont Harbor for a 40 footer is pushing $5000 when tax is included. That's if you are a Chicago resident - for suburbanites, there is a 25% surcharge. You have to put fuel in the boat from time to time, and they charge for that. In November, the boat has to go to Crowleys and be hauled out for the winter. Then back in the water in May, tuned up for the Spring. And there is maintenance and routine repair, insurance, license fees, taxes, and who knows what else. I'm guessing it all adds up to something in the neighborhood of $10K per year - and that's not even considering the purchase of the boat itself, let alone new sails, etc.
Time-Share: $8550 for the season (the same Jeanneau 40 I leased), plus a refundable damage deposit and a membership fee. That gets you 36 sailing opportunities (9:00 am - 5:00 pm or 5:00 pm - 9:00 am); 14 weekend and 22 weekday. They maintain the boat, top up the water, and pump out the holding tank. Once we were out an noticed a 4" tear in the foresail - we put it down in the log and the next time we showed up there was a new sail.
All you do is show up and sail.
Clearly, if you are retired and have nothing interesting to do except sail, six times sailing each month isn't going to seem like much. But if you only have time to sail once or twice per week, this is a fine option - and it costs less than what you would pay as an boat owner. If you can live with a (mere?) 37 footer, it is even less expensive.
[not affiliated with Pinnacle, just a satisfied client]