Here was my experience(s) with the designated lodging...
1. There were never enough rooms for everyone. As soon as the meeting was over people would rush home to call the hotels of their first choice. Then cell phones came along...people started calling from the parking lot as soon as the meeting was over. So then the WTS said... no calling before noon the next day. But - there was always one or two congregations that had the service meeting earlier in the week than the rest of us...those slimy bastards got a two day head start on the rest of us...so we would bug friends from that cong. to make a list and give it to us so we could make arrangements before we ever had our meeting. Nothing says Christian love like beating your Christian brother to the lodging list and getting the choice rooms first...
2. After awhile we tired of fighting for a medicore room in a mediocre hotel... so we started making our own arrangements. Due to our circumstances at the time, we could actually get deeper discounts than what the WTS could get. We thought this was a good thing for all concenred. Since there wasn't enough rooms for everyone, we're not taking up a room that some other family that didn't have any other discounts available could use. A benefit to us was that we could pick the hotel of our choice, nice restaurant and bar being pre-requisites to enjoying our stay for 4 days. Of course, we got counsled for not following WT rules. We were not, under any circumstance, to make our own arrangements. If the rooms were all gone, then we were supposed to wait on the Society to release a second list (which invariably had even worse hotels on the list)
3. On more than one occasion, a hotel was so dirty/disgusting/nasty/revolting that the JWs complained so loudly to the rooming department that they had to relocate an entire hotel full of people duing the middle of the convention.
4. By the time I had mentally checked out, I didn't care what the rules were. I knew what hotel I liked best and that's where I was staying. If all the JW rooms were gone, I booked anyway. When the hotel gave up working with the WTS and it was no longer on the list, I stayed there anyway. And I wasn't alone... I noticed lots of dubs staying there as well.
5. But there were good times as well...when I was a teenager/early 20something; a group of us would book a room, even though we lived in a convention city at that time, just so we could party for 4 days. We always put 6 to 8 people in a room, brought booze in, had drinking games, played poker, watched porn, generally had a great time. We got busted one time when hotel cameras caught multiple people coming and going out of one room so they had security check it out and realized we had 8 people sleeping in the room. Then there was the time that a party went bad and the elders got wind of it and went on a witch hunt. DFings/reprovals were handed down. I quit staying with that group after that because loose lips sink ships and too many people had big mouths. Better to party with a small group that you can trust instead of a large group where you don't know everyone.