The red and black wires are the track pickups. The red one is generally connected to the loco pickups and the black one to the tender pickups. For the gray and orange to the motor, the orange most often goes to the engineer side for the default forward direction. It makes no difference if the gray and orange are reversed because changing CV29 by one digit will change the normal forward direction.
As Joe mentioned the drawbar is the tender pickup to the loco.
Depending on the loco, you can sometimes fit the decoder in the boiler. I have had no trouble doing that with most of bigger PRR models such mikados and decapods and k4s from USH. I generally stuff it in above the weight.
A drawbar with a whisker implies newer perhaps sunset.
If you can fit decoder into the boiler, you can get by with only one wire from the tender for pickup only. You could use the top of the whisker pin connection. However if you want lights on the tender you need a wire for each light plus the ground. Most of mine have back up lights so I use 3 wires - black for the track to the decoder and yellow for the backup light, and blue for the light common.
I generally do not use the pin, I use a 3 wire plug and socket.
Now if you have to put the decoder in the tender, you probably need 5 wires to the loco. You need one for the red wire for the track pickups from the loco. Then you need 2 for the gray and orange to the motor. And 2 more for the headlight, white and blue. You will need to get a 5 pin plug. Micromark and Tony's train exchange sell them by the pin - you can get a strip of the 36 and cut your own.
Use a light soldering iron when working with these plugs and sockets because it is easy to melt the plastic. I seal the joints with shrink tubing too.
By the way, I have done a bunch of these and I really lke the decoder for motor control. Also if you burn out a light function, there 3 at least additional you can reprogram for front or rear lights.