The only way to get the full HUD is to play in software mode. I think that it's always been that way.

Software mode is choosing dgVoodoo Virtual SVGA Card under Direct X in the wrapper right? just doesn't seem to work for me.

That forces the game to run unaccelerated (i.e. in software), but it's still using its Direct3D renderer, and the full HUD is disabled when that's used. You need to make the game use its original software ("GDI") renderer. You do that by running olcfg.exe and choosing Window. Unfortunately, that means playing in a window, but the bigger issue (that I just discovered, or else I would've said so earlier) is that it doesn't capture the mouse, so it's not even playable unless you play only with the keyboard. Unless someone has found a solution, I guess that there's no good way to play the game with the original HUD on modern Windows (unless you set up a virtual 95/98/XP installation).

https://www.gog.com/forum/outlaws_a_handful_of_missions/how_to_fix_software_rendeningdirectdraw_mode_use_this_only_if_lecddrawdll_is_missing

This works 100% in 4:3 fullscreen (1440x1080) and 16:9 fullscreen (1920x1080). make sure you use dgVoodoo 2.54 as newer versions cause problems with this game.

Did anyone mention you need to have the ( Nglide - wrapper ) installed . ?

Nglide is included in the GOG installer by default. But it does make the game look worse because of texture filtering. Wish Nglide would finally have the option to turn that shit off. Also you can't have the full hud when using Nglide because it was slightly modified.

The screens I made are dgVoodoo with DirectX active btw. You don't need Nglide for this to work.