So would a motor with a larger I.D. stinger need a larger main jet than a standard size stinger?
I need more information to answer that question. I will give some examples and trends in jetting with changes in pipe back pressure.
Engine package #1:
We have a highly developed engine package where the ports, pipe, head, etc are all optimized to work with each other. This engine package produces good power over a wide RPM range. The back pressure in the pipe for this engine package is optimized so that reducing the inside diameter another 0.5mm will cause the engine to experience detonation. Lets say that this engine needs a 180 main jet with a 26.0 mm id stinger
Engine package #2 as compared to engine package #1
We take engine package #1 and increase the ID of the stinger and silencer to 27.0mm. The 180 main jet will be too lean and it may take a 190 main jet to optimize the wide open throttle mixture and power. The power may come on 100 to 300 RPM lower, peak HP may go down and over rev may suffer as much as 300 to 500 RPM after the main jet is optimized.
Engine package #3 as compared to engine package #1
We take engine package #1 and reduce the ID of the stinger and silencer to 25.5 mm. The power may come on 50 to 100 RPM later, peak HP is about the same and over rev may increase as much as 50 to 100 RPM. The 180 main jet produces the best power but 5 to 10 seconds of full throttle will drive the engine into runaway detonation. Installing a 182 main jet makes the detonation go away, the front side (power before the power peak) of the power curve looks good like the power curve from engine package #1 but be loose 300 to 500 RPM on the over rev.
Engine package #4 as compared to engine package #1
We take engine package #1 and reduce the ID of the stinger and silencer to 25.0mm. The power may come on 100 to 300 RPM later, peak HP is down, over rev is down as much as 100 to 400 RPM with a rich misfire at extreme high RPM. We have to reduce the main jet to a 170 to get rid of the rich misfire at the extreme high RPM range but now the engine is experiencing detonation at wide open throttle, engine coolant temperatures have risen substantially, piston crown temperatures can rise to the point of caving in the top of the piston or burning a hole in the middle of the piston in as little as 10 to 15 seconds of full throttle.
In summary:
The restriction or back pressure on a pipe has to be optimized for the amount of power and RPM an engine produces. Go to large on the stinger for you engine package and it will need larger jets and peak power and over rev will be reduced. Go slightly too small on the stinger and the power does not usually change much but the engine is very sensitive to jetting and is always trying to hurt a piston. Go extremely small on the stinger or instal an ill-designed spark arrestor or have a spark arrestor that is partially plugged and you will have to reduce the jet size to keep it from having a rich misfire at the high RPMs. Once the main jet size is reduced to make it not misfire at high RPM the engine seems lazy and is trying to hurt pistons.