Any% route

Settings: For maximum speed, playing in UrQuan's version of ScummVM with speed throttling disabled (and the mouse disabled for DOS authenticity) is recommended. If you play in DOSBox instead., set your configuration to machine=tandy (faster than vgaonly and much faster than the default svga_s3), core=dynamic (faster than the default auto) and cycles=max. The choice of emulator does not affect the route.

Create a savefile called "%v201", and use that every time you save the game. This lets you peek into apple guy RNG.

Numbers correspond to numpad keys, and are used to zip in specific directions.
Commands are indicated in uppercase for clarity, but need not be typed in uppercase.
"ADD" can be used as a synonym for "PUT" throughout.
Press/hold Enter as needed.

8 [select Fastest from menu] OPEN DOOR
9627 SIT [] SHOT [wait for bartender, preparing the next command] YO UP
274981 YO ROSE 6 OPEN DOOR 6 YO RING 4 OPEN DOOR 3 PUT EAT [hold Enter, prep "bang", Enter that too]
72716 F3 [] AL SENT ME [] USE REMOTE [] MOVE CHANNEL (x7 - use F3 to repeat)
2678471629 YO BOX 176 LIFT PANE [] EXI[F3] (or GO  F3 with min. 2 spaces)
4 YO HAMMER [] GO 4 CAB 271 GO
HOTEL [wait] PAY [] GO [F10] (east a bit, north) [Fastest] YO CARD
362 USE SLOT [Enter 2x, F6 19x, keep saving after wins (unless YOLOing), restore on losses, aim for $250]
4 F10 3 [out, CAB, 5, Fastest, F5. Every time you enter this screen from the hotel, if you haven't already met the apple guy, you should save after stopping and calling the cab and note the Y on the "About to save the game described as: XX:Y" screen. If Y is higher than zero, wait for the apple guy to appear, preparing "PAY" as you do; then pay him. If Y is zero, prepare GO instead and forget the apple guy for now.]
2 GO [] DISCO [wait] PAY [] GO [F10, walk to bouncer, PUT PASS; then pass him on the east side, heading north. Fastest. If you aren't taken into the disco, shuffle a bit with 78 or hold 8]
1767 SIT [] SEE HER [] DATE [] GO
[wait] 
397 SIT [the ideal zip here depends on your position after the dance, which is random. Other possibilities include 394, 1767 and 16179] SEE HER
PUT RING [] PUT ROSE [] PUT CANDY [] PUT COIN [] GO
27626 CAB [] GO [] CHAPEL [wait] PAY [] OPEN DOOR
9 F3 8 PAY 
[during a lull in the minister's speech, hit F1, dismiss the help screens, then prepare the command "USE SLOT" and hold Enter]
43183 [F10, north a bit, west, Fastest. The positioning here is fairly precise, and being off by too much will kill you]
[F10] [walk to below hotel door, do apple guy save en route] [north, Fastest]
362 F3 [gamble as before, aim for $70 or above]
4 F10 3 [out, CAB, 5, Fastest, apple guy save]
2 GO [] SHOP [wait] PAY [] GO 
F10 [walk NW, then head towards shop going NE, Fastest] 
98 YO WINE 1 PAY 243 F10 (west to left edge of door, SE, Fastest)
USE PHONE [] 5558039 [be careful with Enter here - holding Enter too much can result in a bad input and require you to call Ajax Liquor a second time, a major time loss]
WINE [] SUITE [] CAB [] PUT WINE [] 92 GO [] HOTEL [wait] PAY [] GO
F10 [east a bit, north, Fastest] 671 FOUR 842424 BANG 
74 YO WINE [] LAY [hit F1, dismiss the help screens] YO KNIFE [] YO ROPE [] 6 OPEN DOOR [] 968393 ONE 8426183 F10 [out, CAB, stop, Fastest, apple guy save]
2 GO [] BAR [wait] PAY [] OPEN DOOR
8 F3 716 BANG [] AL SENT ME 26784716 GO PANE
6 TIE ROPE ME [] TIE ROPE RAIL (use F3 and backspace to replace ME with RAIL) 
YO FLY [] RIP PANE [] YO FLY [] GO RAIL [] YO ROPE
4 GO 4 CAB 271 GO [] HOTEL [wait] PAY [] GO [F10, east, north, Fastest]
671 EIGHT [] 86262 SEE HER [] PUT F3 FLY [hold Enter]
PUSH KNOB [] 86724 GO [invoke help page so you can prepare the next command while waiting] SEE HER [] PUT APPLE

Alternative approaches: It is possible to combine the second gambling round with the visit to the honeymoon suite, but this requires very lucky taxi fare RNG or your money will run out. (Even if it works, the second gambling round must be started with less money.)

SantaClaus

Leisure Suit Larry in the Land of the Lounge Lizards

MS-DOS

swimfan

Native

ScummVM

DOSBox

UrQuan ScummVM

Emulation

Leisure Suit Larry

Timing start rule unclear

Steam version?

Unthrottled AGI in ScummVM?

Cycles amount in DOSBox question

Bigmanjapan

El-Nino

realneuromancer

JeffLane22

jesternario