NaN
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Strategy: Maximize total days off

With NaN days, you can get 40 days off

40 days off
Jan 1 — Jan 33 days (1 vacation)
3.0x
Jan 6 — Jan 94 days (1 vacation)
4.0x
Apr 14 — Apr 174 days (1 vacation)
4.0x
Apr 29 — May 35 days (1 vacation)
5.0x
Jun 2 — Jun 43 days (1 vacation)
3.0x
Jun 15 — Jun 184 days (1 vacation)
4.0x
Aug 12 — Aug 154 days (1 vacation)
4.0x
Oct 28 — Nov 15 days (2 vacation)
2.5x
Nov 10 — Nov 123 days (1 vacation)
3.0x
Dec 22 — Dec 265 days (1 vacation)
5.0x

Strategy: Maximize longest block

With NaN days, you can get 76 days off

76 days off
Jan 1 — Jan 99 days (4 vacation)
2.3x
Apr 15 — Apr 239 days (4 vacation)
2.3x
Apr 29 — May 79 days (3 vacation)
3.0x
May 30 — Jun 46 days (4 vacation)
1.5x
Jun 10 — Jun 189 days (4 vacation)
2.3x
Aug 12 — Aug 209 days (4 vacation)
2.3x
Oct 28 — Nov 59 days (4 vacation)
2.3x
Nov 7 — Nov 126 days (4 vacation)
1.5x
Dec 22 — Dec 3110 days (4 vacation)
2.5x