Nothing new here, but repeating for emphasis:
- Having to unpack/repack isn't much of a con, unless you pack heavily and like to spread loose items around the room. My family packs light (a single 21" bag apiece for trips of up to a week or more), uses color-coded packing cubes and zipper pouches for everything so that "unpacking" is as simple as unzipping cubes and placing them in drawers, with toiletry bags by the sink, pouches with electronics/chargers on the media cabinets or bedside tables, and breakfast foodstuffs and snacks in their own pre-packed folding rectangular bin by the coffeemaker/fridge. Packing up again, we just do the reverse , sweep the room for leftover items, and discard any perishable leftovers from the fridge, and we're good to go in all of 5 minutes.
- Not getting into your room until after 4pm can be a con, if you don't otherwise plan your day around the switch. (Also, anecdotally, DVC seems to be unusually glitchy when it comes to online checkin, and at least one CM told us that this is because their "system doesn't like split stays." (!??!) There have been multiple occasions where we never got a "room ready" text and had to go to the front desk to get our room assignment, even if the room had been ready for hours, so if you don't get one by the time you arrive at your second hotel, don't assume you don't actually have a room yet: check with the front desk.) We drop our packed bags off at Bell Services for transfer first thing in the morning, head to a park for rope drop, and plan a leisurely touring day with TS lunch and dinner reservations in the parks (or sometimes, dinner back at the hotel we're checking into) so that we can feel refreshed and energetic even without our usual daily nap/swim break. Since we're not attempting to check into the hotel until after dinner, we can rest assured that our room will be ready and our luggage will have arrived at Bell Services.
- The biggest con, and the one that has impacted us the most (although it's still not a huge deal as far as I'm concerned), is the unavailability of refrigerated grocery transfers. In order to minimize food waste, we simply start the week with just enough perishables (milk, cream cheese, etc.) to last for the first half of our split stay. For the second half, we either order a second small grocery delivery, or buy what we need in the resort grab-and-go market. All the non-perishables (including any leftover bottled water) get packed in my suitcase for the transfer.
- The multiple ADR windows can be a pain if there are any high-demand ADRs you want. If that's an issue, I suggest making a room-only reservation for a cheap room at a value resort that covers the dates of both split stays -- only those dates, and only do it if your split stay is a contiguous onsite stay with no intervening nights off-site. Then, cancel it without penalty (getting the full deposit back) as soon as you are less than 60 days away from your second split stay checkin date. The ADRs will stay in the system. (*Note: There are folks who disapprove of this practice, but Disney has no rule against it. In fact, some guest services CMs -- it all depends on who answers the phone -- will even help make these kinds of dummy reservations, in order to compensate for the fact that Disney's reservation system isn't capable of recognizing split stays as a contiguous stay onsite, for purposes of the 60+10 day ADR window to which onsite Disney Resorts guests are entitled.)
Also, I always bring a sturdy folding zippable tote bag (my current favorite is the Large-size L.L. Bean "Everyday Lightweight Tote") in my suitcase, which gets used as: (1) a beach bag when we visit the pools; (2) an overflow bag for souvenirs on the trip home, which one of my kids can bring on the plane as their "personal item"; and (3) a "split stay" bag to hold extra non-perishable groceries, souvenirs, or other items that we've acquired during the first half of a split stay, that need to be contained for transfer to the next hotel.