Secondary Input for Part 2:
 

"ATT Conference on 21st" 12 14
"ATT Conference on 22nd" 12 14
"ATT Conference on 23rd" 12 14
"ATT Conference on 24th" 34 36
"Meeting on 23rd" 12 34
"Meeting on 28th" 24 46
"Meeting on 30th" 46 48
"Meeting on 1st" 23 89
"Meeting on 10th" 67 90
"Meeting on 12th" 26 38
"Meeting on 14th" 80 120
"Trip to Florida" 13 25
"Trip to Scotland" 23 46
"Trip to Egypt" 34 125
"Trip to Equador" 67 68
"Trip to Brazil" 78 80
"Trip to Japan" 34 110
"Trip to Australia" 56 57
"B11 Summit 1" 45 46
"B11 Summit 2" 46 47
"B11 Summit 3" 47 48
"B11 Summit 4" 48 49
 

Model Output for Secondary Input:
 

Overflow when trying to insert "ATT Conference on 24th"
Overflow when trying to insert "Meeting on 14th"

 Bucket 1:

      1 "ATT Conference on 21st"
      2 "ATT Conference on 22nd"
      3 "ATT Conference on 23rd"

 Bucket 5:

      15 "Trip to Equador"
      16 "Trip to Brazil"
      17 "Trip to Japan"

 Bucket 6:

      19 "B11 Summit 1"
      20 "B11 Summit 2"
      21 "B11 Summit 3"

 Bucket 7:

      22 "B11 Summit 4"

 Bucket 19:

      8 "Meeting on 1st"
      9 "Meeting on 10th"
      10 "Meeting on 12th"

 Bucket 24:

      12 "Trip to Florida"
      13 "Trip to Scotland"
      14 "Trip to Egypt"

 Bucket 36:

      18 "Trip to Australia"

 Bucket 44:

      5 "Meeting on 23rd"
      6 "Meeting on 28th"
      7 "Meeting on 30th"