is it possible to do multiple SDCs for one reservation
 

I'm on a 6am flight but need to delay departure as much as possible due to work (ideally get on 9pm flight). Can I call at 5am to switch to the 8am, then again at 7am to the 10am, all the way down to the 9pm? I would really not prefer to pay the change fee since i'm not sure that I will even be able to make it out at all! There is loads of availability tomorrow on all the flights (which I know could change, but it's a risk that I will take). Anyone know?

Yes. Just be aware that even flights with good availability the night before can have limited availability the next day due to rebookings, etc. Be careful.

You can SDC as many times as you want. You may want to do it online via OLCI, instead of calling, to save time.

I didnt know you could SDC online during checkin?

But be careful when just looking at options at OLCI or using the kiosks, lots of horror stories of folks just checking options out and getting booted from their seats or worse, F seat.

That's why I continue to call or use the SC, because I have ZERO trust in DL IT.

ugg, moot point. work is preventing me from taking this trip. oh well. there will be plenty of other parties to fly out for. but, good to know that you can SDC more than once!

You CAN SDC as many times as you need/want to. But, be aware that you don't HAVE to SDC more than ONCE in order to do what you need.

Your post makes it sound as if you feel that in order to SDC from an early flight to a later flight, you need to keep jumping to the 'next flight' every 2-3 hours all day long until you get on the 6 PM flight. Not the case.

To SDC from the 6 AM flight to the 6 PM flight, simply MISS the 6 AM flight (doesn't matter if you're checked in or not, as a courtesy, if i have checked in I call delta to have them uncheck me so the seat can be more easily reused.) Then, at 3 PM call in and SDC to the 6 PM flight. That's all...

When doing an early to late SDC, you always run the risk of an IROP wiping out availability on the later flight. So, check and double check availability (expert flyer is the most reliable too for this, but there are others.)

John

Best to confirm status with the agent at the gate or via the displays at the gate. A phone call to customer service is the most reliable method for all things same day.