We just got back from an 8 night trip at 2 resorts, with 6 segments, and using multiple dining plans:
Night 1 - OKW, QS plan
Night 2 - OKW, Dlx plan
Night 3 - BLT, Base plan
Night 4 - BLT, Base plan
Nights 5 and 6 - BLT, Dlx plan
Nights 7 and 8 - BLT, Dlx plan
Note that it would've been easier if we could've had Nights 3 and 4 as 1 segment, then nights 5 through 8 as another segment. But 3 and 4 were segmented due to points used from different use years (May 31st vs June 1st), then nights 7 and 8 we were on a waitlist and when that came through, it automatically stayed as a different segment.
Overall review - it was great being able to pick the dining plan we wanted, I would do it again. Learned my lesson though, instead of 1 QS, 2 base, and 5 dlx -- woudve done 1 QS, 4 base, and 3 dlx nights.
This is our 2nd time using multiple dining plans (although this one was definitely more involved) and servers were still very confused by the "DVC Multiple" statement on our keys - some refused to believe we were on dining plans. Each time, we told them to check and they would come back with a different attitude.
At OKW, we needed new keys on night 2. At BLT, we kept the same keys throughout the stay although we got automated message several times saying we needed new keys. We'd call the front desk, and they'd say we were fine.
A minor glitch I experienced is that I thought the OKW credits would remain on the OKW room keys when we moved to BLT, but when we went to pay for lunch after night 2, our OKW room keys were already inactive. We had to call the resort and the credits were posted manually. When we picked up our keys at BLT, our OKW leftover credits were posted together with our new BLT credits.
With each segment, we would get our credits (automatically at 11 am ET while we were at BLT) -- i.e. for nights 5 and 6, we were credited with the deluxe, snack and mug credits for those 2 nights. We were told at the front desk, however, that those credits would not expire until the end of our stay because we had the deluxe plan for nights 7 and 8 as well. I did NOT test this theory on purpose as I didn't want to spend any extra time at the front desk just in case. However, somehow during nights 5 and 6, a restaurant didn't pull the right number of deluxe credits and our balance showed more than it should've. Those extra credits continued to show through the last day of our stay (I didn't spend it, hoping they would figure it out at some point) so I guess what we were told at the front desk about expiration was correct.
Interesting note - we got refillable mug credits even with the last segment. I thought since we had 4 straight nights of the deluxe plan, we would only be credited mugs on the first night. But since these were split up into 2 two night segments, we ended up with yet another 4 mug credits for our party of 4 during the last 2 night stay. Yes, we ended up with 16 mugs for this trip -- I gave 3 away during the trip, and I think we may give a few more away to the kids' teachers
Hope this helps someone. Any questions, let me know.
Night 1 - OKW, QS plan
Night 2 - OKW, Dlx plan
Night 3 - BLT, Base plan
Night 4 - BLT, Base plan
Nights 5 and 6 - BLT, Dlx plan
Nights 7 and 8 - BLT, Dlx plan
Note that it would've been easier if we could've had Nights 3 and 4 as 1 segment, then nights 5 through 8 as another segment. But 3 and 4 were segmented due to points used from different use years (May 31st vs June 1st), then nights 7 and 8 we were on a waitlist and when that came through, it automatically stayed as a different segment.
Overall review - it was great being able to pick the dining plan we wanted, I would do it again. Learned my lesson though, instead of 1 QS, 2 base, and 5 dlx -- woudve done 1 QS, 4 base, and 3 dlx nights.
This is our 2nd time using multiple dining plans (although this one was definitely more involved) and servers were still very confused by the "DVC Multiple" statement on our keys - some refused to believe we were on dining plans. Each time, we told them to check and they would come back with a different attitude.
At OKW, we needed new keys on night 2. At BLT, we kept the same keys throughout the stay although we got automated message several times saying we needed new keys. We'd call the front desk, and they'd say we were fine.
A minor glitch I experienced is that I thought the OKW credits would remain on the OKW room keys when we moved to BLT, but when we went to pay for lunch after night 2, our OKW room keys were already inactive. We had to call the resort and the credits were posted manually. When we picked up our keys at BLT, our OKW leftover credits were posted together with our new BLT credits.
With each segment, we would get our credits (automatically at 11 am ET while we were at BLT) -- i.e. for nights 5 and 6, we were credited with the deluxe, snack and mug credits for those 2 nights. We were told at the front desk, however, that those credits would not expire until the end of our stay because we had the deluxe plan for nights 7 and 8 as well. I did NOT test this theory on purpose as I didn't want to spend any extra time at the front desk just in case. However, somehow during nights 5 and 6, a restaurant didn't pull the right number of deluxe credits and our balance showed more than it should've. Those extra credits continued to show through the last day of our stay (I didn't spend it, hoping they would figure it out at some point) so I guess what we were told at the front desk about expiration was correct.
Interesting note - we got refillable mug credits even with the last segment. I thought since we had 4 straight nights of the deluxe plan, we would only be credited mugs on the first night. But since these were split up into 2 two night segments, we ended up with yet another 4 mug credits for our party of 4 during the last 2 night stay. Yes, we ended up with 16 mugs for this trip -- I gave 3 away during the trip, and I think we may give a few more away to the kids' teachers

Hope this helps someone. Any questions, let me know.
Bill