Oh..something else to know/keep in mind...

When you do these sorta trips it is important to look at the exact routing and aircraft type. If your incoming flight is late you can get stranded and it can be a mess...

In the case above, your flight is to SJC which is NOT a hub or a focus city, so normally there would be a big risk that if your flight TO SJC were late, you would miss your flight FROM SJC...

HOWEVER...back at the itasofware.com step...when you select the specific route/ticket/price for the day that you selected...it confirms the flight from MSP to SJC is a A320 and the flight FROM SJC to MSP is also an A320... This means it is in face the same plane and it does a turn at SJC, in fact it is probably the exact same crew.

With Delta when you check in they will NOT give you all your boarding passes. When you arrive at your destination, SJC, you will THEN be able to get your return boarding passes. To do this DO NOT leave security...you can simply ask at the gate right when you leave the plane for your boarding pass.

They might give you a weird look, or ask how you got past security without one, but just tell them the truth, you just arrived on the incoming flight and you are returning on the outgoing flight...they should be pretty familiar with the MR concept....but if not just say "I am flying to make sure I keep my status next year"

I personally have done this exact same thing to SJC when they use to have Delta service from ATL to SJC and then a red-eye back from SJC...

Good luck!