NaN
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Strategy: Maximize total days off

With NaN days, you can get 43 days off

43 days off
Jan 1 — Jan 44 days (1 vacation)
4.0x
Mar 13 — Mar 175 days (2 vacation)
2.5x
Mar 25 — Mar 295 days (1 vacation)
5.0x
Apr 30 — May 34 days (1 vacation)
4.0x
May 28 — May 314 days (1 vacation)
4.0x
Jul 9 — Jul 124 days (1 vacation)
4.0x
Jul 30 — Aug 24 days (1 vacation)
4.0x
Aug 27 — Aug 304 days (1 vacation)
4.0x
Nov 27 — Nov 304 days (1 vacation)
4.0x
Dec 24 — Dec 285 days (1 vacation)
5.0x

Strategy: Maximize longest block

With NaN days, you can get 87 days off

87 days off
Jan 1 — Jan 77 days (4 vacation)
1.8x
Mar 13 — Mar 186 days (3 vacation)
2.0x
Mar 20 — Mar 2910 days (4 vacation)
2.5x
May 1 — May 99 days (4 vacation)
2.3x
May 29 — Jun 69 days (4 vacation)
2.3x
Jul 10 — Jul 189 days (4 vacation)
2.3x
Jul 31 — Aug 89 days (4 vacation)
2.3x
Aug 28 — Sep 59 days (4 vacation)
2.3x
Nov 27 — Dec 59 days (4 vacation)
2.3x
Dec 24 — Jan 210 days (4 vacation)
2.5x