Baseline - Typical strats, equipment, three herbs Win Difference vs -4 HP Win Difference vs -2 Strength
Wins (Out of 1,000) Wins (Out of 1,000) Wins (Out of 1,000)
Str 18 222 306 384 400 458 449 502 Str 18   84 78 16 58 -9 53 Str 18              
20 275 342 407 455 453 525 526 20   67 65 48 -2 72 1 20 53 36 23 55 -5 76 24
22 295 396 390 461 499 487 536 22   101 -6 71 38 -12 49 22 20 54 -17 6 46 -38 10
24 320 364 448 470 523 553 577 24   44 84 22 53 30 24 24 25 -32 58 9 24 66 41
26 336 413 476 524 556 581 615 26   77 63 48 32 25 34 26 16 49 28 54 33 28 38
40 44 48 52 56 60 64 40 44 48 52 56 60 64 40 44 48 52 56 60 64
HP HP HP
To be clear: Inventory is Leather Armor, Wooden Hat, Scale Shield, Sword of Malice, Flying Shoes, Medical Herb x3.  These stats represent a range of bad level 6 stats to good level 7 stats.  Healie has full HP and MP.
A and Pray - No parrying, no herbs, typical equip Comparison to Baseline
Wins (Out of 1,000) Wins (Out of 1,000)
Str 18 153 239 266 284 351 371 391 Str 18 -69 -67 -118 -116 -107 -78 -111
20 183 240 299 338 336 389 455 20 -92 -102 -108 -117 -117 -136 -71
22 194 287 286 338 376 406 478 22 -101 -109 -104 -123 -123 -81 -58
24 207 287 337 367 378 411 463 24 -113 -77 -111 -103 -145 -142 -114
26 205 295 370 380 450 479 473 26 -131 -118 -106 -144 -106 -102 -142
40 44 48 52 56 60 64 40 44 48 52 56 60 64
HP HP
No Parrying, Typical Equip Comparison to Baseline
Wins (Out of 1,000) Wins (Out of 1,000)
Str 18 227 256 348 373 400 451 456 Str 18 5 -50 -36 -27 -58 2 -46
20 217 293 380 386 458 501 505 20 -58 -49 -27 -69 5 -24 -21
22 222 318 362 407 470 473 535 22 -73 -78 -28 -54 -29 -14 -1
24 236 282 411 423 482 538 541 24 -84 -82 -37 -47 -41 -15 -36
26 297 362 418 447 502 564 589 26 -39 -51 -58 -77 -54 -17 -26
40 44 48 52 56 60 64 40 44 48 52 56 60 64
HP HP
No Herbs, Typical Equip Comparison to Baseline
Wins (Out of 1,000) Wins (Out of 1,000)
Str 18 204 233 278 323 364 384 416 Str 18 -18 -73 -106 -77 -94 -65 -86
20 213 268 327 372 378 385 431 20 -62 -74 -80 -83 -75 -140 -95
22 253 285 353 394 384 457 462 22 -42 -111 -37 -67 -115 -30 -74
24 233 318 361 392 423 474 458 24 -87 -46 -87 -78 -100 -79 -119
26 245 329 348 434 463 460 491 26 -91 -84 -128 -90 -93 -121 -124
40 44 48 52 56 60 64 40 44 48 52 56 60 64
HP HP
Max Herbs: Iron Armor, Sword of Malice, Shoes, and Five Herbs Comparison to Baseline
Wins (Out of 1,000) Wins (Out of 1,000)
Str 18 255 353 362 410 464 491 490 Str 18 33 47 -22 10 6 42 -12
20 296 399 413 453 509 544 570 20 21 57 6 -2 56 19 44
22 295 418 468 494 534 533 591 22 0 22 78 33 35 46 55
24 339 419 445 514 527 593 553 24 19 55 -3 44 4 40 -24
26 369 407 487 545 585 618 650 26 33 -6 11 21 29 37 35
40 44 48 52 56 60 64 40 44 48 52 56 60 64
HP HP
Bronze Armor would be five defense power less and only require one of the two gold chests.
Max* Armor: Iron Armor replaces Leather Armor Comparison to Baseline Comparison to Two Baseline Attempts
Wins (Out of 1,000) Wins (Out of 1,000) Wins (Out of 1,000)
Str 18 358 384 430 527 523 534 566 Str 18 136 78 46 127 65 85 64 Str 18 -37 -134 -191 -113 -183 -162 -186
20 357 443 489 529 582 566 612 20 82 101 82 74 129 41 86 20 -117 -124 -159 -174 -119 -208 -163
22 380 465 554 542 617 630 658 22 85 69 164 81 118 143 122 22 -123 -170 -74 -167 -132 -107 -127
24 427 491 520 580 572 595 662 24 107 127 72 110 49 42 85 24 -111 -105 -175 -139 -200 -205 -159
26 453 540 586 610 675 660 702 26 117 127 110 86 119 79 87 26 -106 -115 -139 -163 -128 -164 -150
40 44 48 52 56 60 64 40 44 48 52 56 60 64 40 44 48 52 56 60 64
HP HP HP
* I didn't replace Scale Shield with Iron Shield because it cost too much.  Big win chance boost, but you can make an extra Shadow attempt in the time it takes to get both gold chests to afford all this. There's a big deficit here, but the more attempts you make, the more it evens outc But I'm not thinking this is ever worth it.  You'd have to make like four runs with the big armor vs five runs with the usual before this wins.