While held back by cumbersome poorly aged controls and clunky hard to decipher combat, along with a fair dose of Adventure Game Logic, Redguard is far too charming an adventure to skip entirely and should be experienced at least in some way by any Elder Scrolls fan.
That said, should you play it yourself? The depends. If you've got an actual machine of the era laying around, or you're very well versed in either running old games in virtual machines or manually configuring different DOSBox forks and dgVoodoo to get it running properly in Glide mode, then definitely! But if you're not familiar with troubleshooting and getting old Windows 3.1 games to run on modern computers then I'd say not much is lost by watching a playthrough on YouTube rather than playing it yourself, the game as it's packaged on Steam and GoG comes in a pretty sorry state out of the box.
That said, should you play it yourself? The depends. If you've got an actual machine of the era laying around, or you're very well versed in either running old games in virtual machines or manually configuring different DOSBox forks and dgVoodoo to get it running properly in Glide mode, then definitely! But if you're not familiar with troubleshooting and getting old Windows 3.1 games to run on modern computers then I'd say not much is lost by watching a playthrough on YouTube rather than playing it yourself, the game as it's packaged on Steam and GoG comes in a pretty sorry state out of the box.