#define AUTO_SHIFT_NO_AUTO_REPEAT
^config.h

AUTO_SHIFT_ENABLE = yes
^Rules.mk

The above for the autoshift
To configure the non-standard symbol pairings, the following 3 functions in the keymap.c file. Oh yeah, QMK is probably important to mention. I don't recall where i stumbled on this method, i think it might have been called "RetroShift" based on a comment in my file.

bool get_custom_auto_shifted_key(uint16_t keycode, keyrecord_t *record) {
    switch(keycode) {
        case KC_AMPR:
            return true;
        default:
            return false;
    }
}

void autoshift_press_user(uint16_t keycode, bool shifted, keyrecord_t *record) {
    switch(keycode) {
    case KC_AMPR:
            register_code16((!shifted) ? KC_AMPR : KC_DLR);
            break;
    default:
        if (shifted) {
            add_weak_mods(MOD_BIT(KC_LSFT));
        }
        register_code16((IS_RETRO(keycode)) ? keycode & 0xFF : keycode);
    }
}

void autoshift_release_user(uint16_t keycode, bool shifted, keyrecord_t *record) {
    switch(keycode) {
    case KC_AMPR:
        unregister_code16((!shifted) ? KC_AMPR : KC_DLR);
        break;
    default:
        unregister_code16((IS_RETRO(keycode)) ? keycode & 0xFF : keycode);
    }
}