By neildaemond, an 'any-stack' hacking grasshopper.
Taking notes while tinkering with:

Webpack File Loader to Custom Load Path

So, I asked on freenode ( #webpack ) and realised the answer before I could hear a response

│18:10:30 neildaemond | using this webpack.config.js, I end up with some files  │
│                     | like "27474d2c2aa69b9fff15b5748ef7be30.gif".. It all    │
│                     | works, but on the web server I want them to load from   │
│                     | another location like "domain.com/another/custom/path/2 │
│                     | 7474d2c2aa69b9fff15b5748ef7be30.gif", not at root       │
│                     | (domain.com/27474d2c2aa69b9fff15b5748ef7be30.gif)       │
│18:10:48 neildaemond | https://pastebin.com/AJKS9yf7                           │
│18:23:43 neildaemond | oh, I figured it out.. an option for the file-loader.   │
│                     | updated the webpack.config.js to:                       │
│                     | https://pastebin.com/GQvWF9H7                           │

for the record, that second pastebin link just holds:

 1 const path = require('path');
 2
 3 module.exports = {
 4     entry: './src/index.js',
 5     output: {
 6         filename: 'bundle.js',
 7         path: path.resolve(__dirname, 'dist')
 8     },
 9     module: {
10         rules: [
11             {
12                 test: /\.css$/,
13                 use: [
14                     'style-loader',
15                     'css-loader'
16                 ]
17             },
18             {
19                 test: /\.less/,
20                 use: [
21                     {
22                         loader: 'style-loader', // creates style nodes from JS strings
23                     },
24                     {
25                         loader: 'css-loader', // translates CSS into CommonJS
26                     },
27                     {
28                         loader: 'less-loader', // compiles Less to CSS
29                     }
30                 ]
31
32             },
33             {
34                 test: /\.(png|svg|jpg|gif)$/,
35                 use: [
36                     {
37                         loader: 'file-loader',
38                         options: {
39                             outputPath: 'site/templates/design/dist'
40                         }
41                     }
42
43                 ]
44             }
45         ]
46     },
47     watch: true
48 };

#Webpack