no, you are not doomed

Here is an example screenshot of the issue I get when I open the game, very odd this is the only one to give me issues.

It sounds like your shortcut has not changed the current directory to the game directory, so it can't find any files.

This is my current target: "C:\Program Files (x86)\DOSBox-0.74\DOSBox.exe" -userconf "D:\dosgames\hoboken\slh.exe" -exit

All of my other games use the same for shortcuts - different exe's and directories if required obviously, and even when using custom conf files if needed (this one happens to work fine with the main conf file I have setup).

Thanks for any assistance

If it's a CD-ROM game, the CD isn't getting mounted, probably, so instead of doing such a shortcut why not:
"C:\Program Files (x86)\DOSBox-0.74\DOSBox.exe" -userconf -conf "D:\dosgames\hoboken\slh.conf" -exit

And put the appropriate cd mountings and slh.exe in the autoexec section of slh.conf?
If it's not a cd version and it works from the command line, why not try my suggestion anyway?

Your userconf option is not a configuration file, it's trying to run the actual game. That is indeed the current directory problem.
You need to create a config file with an autoexec section that mounts the game directory properly, changes to the game directory, and then runs the .exe (that is, to replicate exactly what you are typing at the command prompt).

Fixed the issue!

Tried it out the suggestion by Bloodbat, and I still got NO graphics but command line still works fine. But the issues I was having appear to be with the Legend.ini file which I guess is the configuration file from the game itself. By default these are the settings for directories:

GAMEDATA=C:\HOBOKEN\
VOCDATA=D:\HOBOKEN\
SAVEDATA=C:\HOBOKEN\

I changed it to the following:

GAMEDATA=D:\HOBOKEN\
VOCDATA=D:\HOBOKEN\
SAVEDATA=C:\HOBOKEN\

And now it works no problem. I just changed the GAMEDATA folder to D:\HOBOKEN, to reflect the mounted CD drive and now it works no problem with a mounted image. Thanks!