Mefordis, I don't blame you for posting that type of question here. For many people going through these message boards, it sounds like free upgrades happen all the time. Unfortunately, that's not exactly true. You just see a lot more posts titled "Free Upgrade" as opposed to "Hey, I got what I paid for"
In your situation, because you have 2 rooms booked, it's probably less likely that you would get a complimentary upgrade. At the YC, the club level is on a higher, secure floor, so if they only upgraded one of your rooms, technically, yourself or the family in the other room wouldn't have access to the lounge. I don't know what you have booked, but basically concierge is $120 more per night than the standard view rack rate. If you have water view booked, then it's closer to $50 more per night. Even if you ask at check-in, I don't think you're going to get an upgrade offer less than that cost. Especially, considering you already have a discounted room... the difference in cost could actually be much higher.
I'd say that if you really want club level, to call now about availability with your current discount. If you're going to ask at check-in, I would be sure that both groups are checking in together and if an upgrade is offered, you need to ask the cost. Some have reported asking for an upgrade, being told that one is available, accepting it and assuming it was complimentary, only to find out it wasn't
. That could be pretty awkward.