Give me the Pros/Cons of doing a Split Stay

We have done many split stays, usually with little problems. For the number of days you are staying a split stay works well without feeling like you are always packing and moving.

On the day we transfer resorts, I will usually go to the new resort and check-in so that we can get our room keys and have the desk send us a text when the room is ready. DH will stay behind to take care of bell services for luggage & grocery transfer. If we are doing a park that day, we will meet at the one closest to the resort we are switching to and I will have an ADR for late lunch either in the park or at that resort. Sometimes, our transfer day is one that we consider a "day off" from parks and will get up a bit later, eat a late breakfast either ADR or grab from a bakery, then go to DTD or resort visiting as we shop. Never feels like a wasted day.

The best advice I can give is to book the last portion of your stay in a resort that you love. That way, if you find that you didn't care so much for one of the other resorts in your stay then you not only have something to look forward to but you can end on a high note.
 
both times we did this we went from OKW to SSR. On SSR check-in day, I made sure I was at the SSR check-in counter at 6 am. Room was ready since I was the only lunatic in the lobby. I took the keys and check-in materials back to OKW and slept a couple of more hours. We then got a luggage cart ride with our bags to SSR, put everything in our room, and went on with our day. OKW and SSR are sister resorts who share many of the same staff members, so I think that made it easier.

I've only done one split stay, more out of necessity than choice due to a last minute trip. I would prefer to only unpack once, but was open to it considering I want to be able to see all the properties that DVC has to offer.

I would second JackDiznee's approach as I did the exact same thing. It also helps to have a car with you. The morning of the move, we got up early, as my wife and kids were packing up, I drove from VWL to SSR to check in and see if a room was available. Fortunately one was, so I went back to VWL and loaded the car move our stuff to SSR and went on to Hollywood Studios.

Had the room not been available, I would have asked Bell Services to move our stuff and gone to the park.

I think you will be fine, just go into it with your expectations in check.
 
Actually moving day we have 2 home resorts-esp when moving to BCV for SAB access as soon as you want.

We always split. Now since BLT we do 1/2 there our nights there (for 5 minute to MK), and 1/2 at BCV (5 minutes to EPCOT). We do AK one 1/2 day so our bus waits/trips are almost nonexistant.

We check out of BLT and the bags are delivered to BCV that afternoon. We monorail to EPCOT like it was a typical day anyway-checkin whenever the 5 minute walk suits us (usually with TT or Soarin FPs for that night). Or lounge at SAB-can't beat that.
 















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